Ethynyl-1,2-benziodoxol-3(1 H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters
Gespeichert in:
| Veröffentlicht in: | Chemistry : a European journal Jg. 16; H. 31; S. 9457 - 9461 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Journal Article |
| Sprache: | Englisch |
| Veröffentlicht: |
Weinheim
WILEY-VCH Verlag
16.08.2010
Wiley Wiley Subscription Services, Inc |
| Schlagworte: | |
| ISSN: | 0947-6539, 1521-3765, 1521-3765 |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| Author | Fernández González, Davinia Brand, Jonathan P. Waser, Jérôme |
|---|---|
| Author_xml | – sequence: 1 givenname: Davinia surname: Fernández González fullname: Fernández González, Davinia organization: Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland), Fax: (+41) 21-693-9700 – sequence: 2 givenname: Jonathan P. surname: Brand fullname: Brand, Jonathan P. organization: Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland), Fax: (+41) 21-693-9700 – sequence: 3 givenname: Jérôme surname: Waser fullname: Waser, Jérôme email: jerome.waser@epfl.ch organization: Laboratory of Catalysis and Organic Synthesis, Ecole Polytechnique Fédérale de Lausanne, EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne (Switzerland), Fax: (+41) 21-693-9700 |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/20645361$$D View this record in MEDLINE/PubMed |
| BookMark | eNqNksFuEzEQhi1URNPAlSOyxIFWdIO93vVmuZXtNkFURUKgcrMc75hsu7GD7VUTTlx5TZ4Eh6Q5VELi4hnZ3z8j_zNH6MBYAwg9p2RECUnfqDksRimJOc1Z-QgNaJ7ShBU8P0ADUmZFwuP9ITry_oYQUnLGnqDDlPAsZ5wO0KoO87VZdwk9TZMZmB-tbezKdgk7pr9__pqeJLEfPq7ffT15i88MrlcKlqG1Rnb4E8hvYALW1uEwB7wrJTfP2Gr8AYI9xdVamhikafBVG5zFtQ_g_FP0WMvOw7NdHKIvF_Xnappcfpy8r84uE8VKHhLaZLJghDe5VoqNSVnQDKCc5YzqUqqSK8WJLous0aDimTJCKZlJInWR8UazIXq1rbt09nsPPohF6xV0nTRgey-KrCRpHg2M5MsH5I3tXfyoF7TgBWNZFr0cohc7qp8toBFL1y6kW4t7SyMw3gJ3MLPaqxaMgj0WZ5CON6PKY0Z51Ya_dlW2NyFKX_-_NNLZllbOeu9AC7WrFpxsO0GJ2KyI2KyI2K9IlI0eyO4b_FOQbAVtHNxqT0t3K6IrRS6urybifJpeTPmEimv2ByohyFA |
| CODEN | CEUJED |
| CitedBy_id | crossref_primary_10_1002_adsc_201400857 crossref_primary_10_1002_chem_201904520 crossref_primary_10_1002_anie_201602783 crossref_primary_10_1002_anie_202014775 crossref_primary_10_1039_C4CC00608A crossref_primary_10_1039_D0QO00203H crossref_primary_10_3762_bjoc_14_107 crossref_primary_10_1002_ejoc_202200516 crossref_primary_10_1021_ja5059795 crossref_primary_10_1021_ja206837j crossref_primary_10_1021_jacs_9b00391 crossref_primary_10_1021_jacs_6b00278 crossref_primary_10_1039_c3cc40529j crossref_primary_10_1126_science_ado0875 crossref_primary_10_1055_a_1984_0686 crossref_primary_10_1002_chem_201900950 crossref_primary_10_1002_chem_201304831 crossref_primary_10_1021_ja206002m crossref_primary_10_1002_ejoc_201100360 crossref_primary_10_1038_s41586_019_1690_5 crossref_primary_10_1002_ange_201509073 crossref_primary_10_1002_anie_201100718 crossref_primary_10_1039_C2CC37281A crossref_primary_10_1002_ejic_202000249 crossref_primary_10_1002_adsc_201401007 crossref_primary_10_1016_j_tetlet_2013_02_023 crossref_primary_10_1039_C5CC03362D crossref_primary_10_1002_ejoc_202100323 crossref_primary_10_1021_jacs_0c08231 crossref_primary_10_1016_j_tetasy_2015_10_006 crossref_primary_10_1021_jo502204a crossref_primary_10_1002_chem_201703238 crossref_primary_10_1021_acscentsci_2c00204 crossref_primary_10_1002_ejoc_201601446 crossref_primary_10_1002_ange_201602783 crossref_primary_10_1002_chem_201501094 crossref_primary_10_1016_j_tet_2018_11_047 crossref_primary_10_1002_anie_201509073 crossref_primary_10_1002_jhet_2624 crossref_primary_10_1039_C5QO00004A crossref_primary_10_1002_anie_201610274 crossref_primary_10_1002_chem_201604475 crossref_primary_10_1038_nature14902 crossref_primary_10_1039_C0CC02265A crossref_primary_10_1002_chem_201200200 crossref_primary_10_1002_adsc_202001264 crossref_primary_10_3390_molecules28052136 crossref_primary_10_1002_ajoc_202300633 crossref_primary_10_1002_ejoc_201600123 crossref_primary_10_1002_cphc_201701339 crossref_primary_10_1016_j_tet_2025_134666 crossref_primary_10_1002_ange_201610274 crossref_primary_10_1002_ange_201505111 crossref_primary_10_1002_chem_201202977 crossref_primary_10_1002_ejoc_202200276 crossref_primary_10_1002_ajoc_202000027 crossref_primary_10_1002_chem_202005124 crossref_primary_10_1002_ejoc_201600253 crossref_primary_10_1002_hlca_201700221 crossref_primary_10_1002_anie_202002626 crossref_primary_10_1016_j_cej_2024_153013 crossref_primary_10_1007_s00726_015_1917_1 crossref_primary_10_1038_ncomms6707 crossref_primary_10_1021_jacs_2c06934 crossref_primary_10_1002_chem_202203997 crossref_primary_10_1002_ange_201100718 crossref_primary_10_1002_ange_202014775 crossref_primary_10_1039_C4OB02625J crossref_primary_10_3762_bjoc_20_127 crossref_primary_10_1002_ceur_202500129 crossref_primary_10_1038_s41467_017_02801_9 crossref_primary_10_1039_c4cc01141d crossref_primary_10_1039_C9SC03033F crossref_primary_10_1002_chem_201703723 crossref_primary_10_1002_ange_201302210 crossref_primary_10_1002_chem_201602622 crossref_primary_10_1039_C4CC06851C crossref_primary_10_1016_j_tetasy_2013_02_008 crossref_primary_10_1002_cctc_201200116 crossref_primary_10_1021_jacs_5b05287 crossref_primary_10_1002_ange_201807418 crossref_primary_10_3762_bjoc_16_45 crossref_primary_10_1016_j_tet_2015_06_053 crossref_primary_10_1021_ja306638s crossref_primary_10_1002_adsc_201300266 crossref_primary_10_1002_anie_201302210 crossref_primary_10_1016_j_tet_2018_04_050 crossref_primary_10_1021_ja4044196 crossref_primary_10_1021_ja5083014 crossref_primary_10_1002_anie_201505111 crossref_primary_10_3762_bjoc_16_251 crossref_primary_10_3390_molecules22071069 crossref_primary_10_1002_ange_201203062 crossref_primary_10_1002_anie_201807418 crossref_primary_10_1039_c2cs35034c crossref_primary_10_1002_ejoc_201700940 crossref_primary_10_1016_j_tet_2017_03_072 crossref_primary_10_1021_jacs_8b05870 crossref_primary_10_1246_bcsj_20220330 crossref_primary_10_1002_chem_201502423 crossref_primary_10_1038_s41570_018_0071_1 crossref_primary_10_1002_ange_202002626 crossref_primary_10_1039_C6QO00631K crossref_primary_10_1039_D1SC04247E crossref_primary_10_1002_anie_201203062 crossref_primary_10_1002_chem_202203986 crossref_primary_10_1007_s00726_016_2276_2 crossref_primary_10_1002_chem_202403654 |
| Cites_doi | 10.1002/chem.200501052 10.1002/ange.200905419 10.1002/ange.19901020317 10.1021/cr800332c 10.1021/ja067289q 10.1021/ol0357907 10.1021/jo00079a046 10.1002/anie.200603497 10.1002/ange.200906755 10.1016/S0040-4039(00)85591-4 10.1039/b807499m 10.1021/jo00137a008 10.1021/ol070447d 10.1016/j.tetlet.2005.12.133 10.1002/ange.200603497 10.1002/adsc.200800776 10.3998/ark.5550190.0004.620 10.1039/B612008C 10.1002/anie.200905419 10.1021/ed082p1833 10.1021/ja909726h 10.1002/anie.200900974 10.1021/jo00074a016 10.1007/3-540-46114-0 10.1039/a608582b 10.1016/S0040-4039(01)94610-6 10.1021/cr050992x 10.1039/a905898b 10.1016/0040-4020(96)00630-8 10.1016/0040-4039(94)02459-O 10.1007/BF00807939 10.1021/ar50106a003 10.1002/ange.200900974 10.1039/a707840d 10.1016/S0040-4039(00)87345-1 10.1016/S0040-4020(98)00410-4 10.1021/ol026050l 10.1039/C39900001100 10.1021/jo00012a025 10.1002/(SICI)1521-3757(19980216)110:4<495::AID-ANGE495>3.0.CO;2-W 10.1039/P19890000333 10.1002/(SICI)1521-3773(19980302)37:4<489::AID-ANIE489>3.0.CO;2-N 10.1021/ol9027286 10.1002/anie.200904689 10.1016/S0040-4020(99)00486-X 10.1002/ange.200904689 10.1002/anie.200604050 10.1021/ja063384n 10.1021/ja910461e 10.1039/c39900000118 10.1021/cr0201068 10.1002/anie.200906755 10.1002/anie.199002871 10.1021/jo01017a053 10.1016/S0040-4039(01)86636-3 10.1246/bcsj.69.2649 10.1002/hlca.19920750622 10.1002/ange.200604050 10.1021/ja00324a025 10.1039/b612008c |
| ContentType | Journal Article |
| Copyright | Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
| Copyright_xml | – notice: Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim |
| DBID | BSCLL AAYXX CITATION 17B 1KM 1KN BLEPL DTL EGQ GIGBA NPM 7SR 8BQ 8FD JG9 K9. 7X8 |
| DOI | 10.1002/chem.201001539 |
| DatabaseName | Istex CrossRef Web of Knowledge Index Chemicus Current Chemical Reactions Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) Web of Science - Science Citation Index Expanded - 2010 PubMed Engineered Materials Abstracts METADEX Technology Research Database Materials Research Database ProQuest Health & Medical Complete (Alumni) MEDLINE - Academic |
| DatabaseTitle | CrossRef Web of Science PubMed Materials Research Database ProQuest Health & Medical Complete (Alumni) Engineered Materials Abstracts Technology Research Database METADEX MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: NPM name: PubMed url: http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=PubMed sourceTypes: Index Database – sequence: 2 dbid: 1KM name: Index Chemicus url: https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database – sequence: 3 dbid: 7X8 name: MEDLINE - Academic url: https://search.proquest.com/medline sourceTypes: Aggregation Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1521-3765 |
| EndPage | 9461 |
| ExternalDocumentID | 3960478991 20645361 000281539500016 10_1002_chem_201001539 ark_67375_WNG_DH2FH6G1_W |
| Genre | Journal Article |
| GrantInformation_xml | – fundername: EPFL – fundername: SNF grantid: 200021_119810 |
| GroupedDBID | --- -DZ -~X .3N .GA .Y3 05W 0R~ 10A 1L6 1OB 1OC 1ZS 29B 31~ 33P 3SF 3WU 4.4 4ZD 50Y 50Z 51W 51X 52M 52N 52O 52P 52S 52T 52U 52W 52X 53G 5GY 5VS 66C 6J9 702 77Q 7PT 8-0 8-1 8-3 8-4 8-5 8UM 930 A03 AAESR AAEVG AAHQN AAMNL AANHP AANLZ AAONW AASGY AAXRX AAYCA AAZKR ABCQN ABCUV ABIJN ABJNI ABLJU ABPVW ACAHQ ACBWZ ACCZN ACGFS ACIWK ACNCT ACPOU ACRPL ACXBN ACXQS ACYXJ ADBBV ADEOM ADIZJ ADKYN ADMGS ADNMO ADOZA ADXAS ADZMN AEGXH AEIGN AEIMD AEUYR AEYWJ AFBPY AFFPM AFGKR AFRAH AFWVQ AFZJQ AGQPQ AGYGG AHBTC AHMBA AITYG AIURR AJXKR ALAGY ALMA_UNASSIGNED_HOLDINGS ALVPJ AMBMR AMYDB ASPBG ATUGU AUFTA AVWKF AZBYB AZFZN AZVAB BAFTC BDRZF BFHJK BHBCM BMNLL BMXJE BNHUX BROTX BRXPI BSCLL BY8 CS3 D-E D-F DCZOG DPXWK DR2 DRFUL DRSTM EBS EJD F00 F01 F04 F5P FEDTE G-S G.N GNP GODZA H.T H.X HBH HF~ HGLYW HHY HHZ HVGLF HZ~ IX1 J0M JPC KQQ LATKE LAW LC2 LC3 LEEKS LH4 LITHE LOXES LP6 LP7 LUTES LW6 LYRES MEWTI MK4 MRFUL MRSTM MSFUL MSSTM MXFUL MXSTM N04 N05 N9A NF~ NNB O66 O9- OIG P2W P2X P4D PQQKQ Q.N Q11 QB0 QRW R.K RNS ROL RX1 RYL SUPJJ TN5 TWZ UB1 UPT V2E V8K W8V W99 WBFHL WBKPD WH7 WIB WIH WIK WJL WOHZO WQJ WXSBR WYISQ XG1 XPP XV2 YZZ ZZTAW ~IA ~WT AAYXX CITATION O8X 17B 1KM 1KN BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE AAHHS ACCFJ ADZOD AEEZP AEQDE AIWBW AJBDE NPM 7SR 8BQ 8FD JG9 K9. 7X8 |
| ID | FETCH-LOGICAL-c396t-1d4a7306d5fcc3809714ee9b531f9ac96cc60f974dfec74d230110ba0af746df3 |
| ISICitedReferencesCount | 167 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000281539500016 |
| ISSN | 0947-6539 1521-3765 |
| IngestDate | Fri Jul 11 16:31:22 EDT 2025 Sat Nov 29 14:35:20 EST 2025 Thu Apr 03 07:09:25 EDT 2025 Wed Jul 09 11:39:34 EDT 2025 Fri Dec 05 23:00:03 EST 2025 Sat Nov 29 07:13:42 EST 2025 Tue Nov 18 22:06:13 EST 2025 Sun Sep 21 06:16:04 EDT 2025 |
| IsDoiOpenAccess | false |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 31 |
| Keywords | ASYMMETRIC-SYNTHESIS hypervalent compounds TERMINAL ACETYLENES umpolung ALPHA-AMINO-ACIDS ALKYNYLIODONIUM SALTS alkynylation DIRECT ALKYNYLATION quaternary carbon atoms HYPERVALENT IODINE REDUCTIVE CLEAVAGE SONOGASHIRA REACTION iodine MICHAEL ACCEPTORS ELECTROPHILIC TRIFLUOROMETHYLATION |
| Language | English |
| License | http://onlinelibrary.wiley.com/termsAndConditions#vor |
| LinkModel | OpenURL |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c396t-1d4a7306d5fcc3809714ee9b531f9ac96cc60f974dfec74d230110ba0af746df3 |
| Notes | istex:2B1A8386D604F5DBBE21C9275C52BF44F58C5A92 EPFL SNF - No. 200021_119810 ark:/67375/WNG-DH2FH6G1-W ArticleID:CHEM201001539 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 14 content type line 23 |
| ORCID | 0000-0002-4570-914X |
| OpenAccessLink | http://infoscience.epfl.ch/record/150505 |
| PMID | 20645361 |
| PQID | 1767334465 |
| PQPubID | 986340 |
| PageCount | 5 |
| ParticipantIDs | crossref_citationtrail_10_1002_chem_201001539 pubmed_primary_20645361 crossref_primary_10_1002_chem_201001539 webofscience_primary_000281539500016 proquest_miscellaneous_749025010 webofscience_primary_000281539500016CitationCount istex_primary_ark_67375_WNG_DH2FH6G1_W proquest_journals_1767334465 |
| PublicationCentury | 2000 |
| PublicationDate | 2010-Aug-16 |
| PublicationDateYYYYMMDD | 2010-08-16 |
| PublicationDate_xml | – month: 08 year: 2010 text: 2010-Aug-16 day: 16 |
| PublicationDecade | 2010 |
| PublicationPlace | Weinheim |
| PublicationPlace_xml | – name: Weinheim – name: WEINHEIM – name: Germany |
| PublicationSubtitle | A European Journal |
| PublicationTitle | Chemistry : a European journal |
| PublicationTitleAbbrev | CHEM-EUR J |
| PublicationTitleAlternate | Chemistry - A European Journal |
| PublicationYear | 2010 |
| Publisher | WILEY-VCH Verlag Wiley Wiley Subscription Services, Inc |
| Publisher_xml | – name: WILEY-VCH Verlag – name: Wiley – name: Wiley Subscription Services, Inc |
| References | T. Wirth, M. Ochiai, V. V. Zhdankin, G. F. Koser, H. Tohma, Y. Kita, Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis, Vol. 224, Springer, Berlin, 2003 T. Kitamura, T. Fukuoka, L. Zheng, T. Fujimoto, H. Taniguchi, Y. Fujiwara, Bull. Chem. Soc. Jpn. 1996, 69, 2649 P. Meffre, L. Gauzy, E. Branquet, P. Durand, F. LeGoffic, Tetrahedron 1996, 52, 11215 F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079 T. Kitamura, K. Nagata, H. Taniguchi, Tetrahedron Lett. 1995, 36, 1081 R. Ciochina, R. B. Grossman, Org. Lett. 2003, 5, 4619. W. D. Sharpless, P. Wu, T. V. Hansen, J. G. Lindberg, J. Chem. Educ. 2005, 82, 1833. No attempt was made to optimize the reaction conditions. Y. Wei, H. Q. Zhao, J. Kan, W. P. Su, M. C. Hong, J. Am. Chem. Soc. 2010, 132, 2522 J. W. Sun, M. P. Conley, L. M. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2006, 128, 9705 P. J. Colson, L. S. Hegedus, J. Org. Chem. 1993, 58, 5918 F. M. Beringer, S. A. Galton, J. Org. Chem. 1965, 30, 1930 E. Dumez, J. P. Dulcere, Chem. Commun. 1998, 479 V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299 S. I. Hashimoto, Y. Miyazaki, T. Shinoda, S. Ikegami, J. Chem. Soc. Chem. Commun. 1990, 1100 K. S. Feldman, ARKIVOC 2003, 179 Y. Nambu, M. Kijima, T. Endo, M. Okawara, J. Org. Chem. 1982, 47, 3066. Angew. Chem. Int. Ed. 2010, 49, 2096, and references therein. B. Witulski, T. Stengel, Angew. Chem. 1998, 110, 495 R. Sauvêtre, J. F. Normant, Tetrahedron Lett. 1982, 23, 4325 I. Kieltsch, P. Eisenberger, A. Togni, Angew. Chem. 2007, 119, 768 Angew. Chem. Int. Ed. 2007, 46, 754 P. Casara, B. W. Metcalf, Tetrahedron Lett. 1978, 19, 1581 A. S. Kende, P. Fludzinski, Tetrahedron Lett. 1982, 23, 2373 A. S. Dudnik, V. Gevorgyan, Angew. Chem. 2010, 122, 2140 S. Nicolai, S. Erard, D. Fernández González, J. Waser, Org. Lett. 2010, 12, 384. Angew. Chem. Int. Ed. 2007, 46, 1018 A. S. Kende, M. Benechie, D. P. Curran, P. Fludzinski, W. Swenson, J. Clardy, Tetrahedron Lett. 1979, 20, 4513 E. Jimenez-Nunez, A. M. Echavarren, Chem. Commun. 2007, 333 C. J. Parkinson, T. W. Hambley, J. T. Pinhey, J. Chem. Soc. Perkin Trans. 1 1997, 1465 J. P. Brand, J. Charpentier, J. Waser, Angew. Chem. 2009, 121, 9510 F. Diederich, P. J. Stang, R. R. Tykwinski, Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH, Weinheim, 2005. V. V. Zhdankin, P. J. Stang, Tetrahedron 1998, 54, 10927 Y. Nishimura, R. Amemiya, M. Yamaguchi, Tetrahedron Lett. 2006, 47, 1839 C. Y. Jin, J. P. Burgess, J. A. Kepler, C. E. Cook, Org. Lett. 2007, 9, 1887. G. E. Keck, T. T. Wager, S. F. McHardy, Tetrahedron 1999, 55, 11755. L. Brandsma, Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques (Best Synthetic Methods Series), Academic Press, New York, 2003. R. Chinchilla, C. Najera, Chem. Rev. 2007, 107, 874. B. M. Trost, A. H. Weiss, Adv. Synth. Catal. 2009, 351, 963. M. D. Bachi, N. Barner, C. M. Crittell, P. J. Stang, B. L. Williamson, J. Org. Chem. 1991, 56, 3912 Angew. Chem. Int. Ed. 2009, 48, 9052. Angew. Chem. Int. Ed. 2009, 48, 4332. Angew. Chem. Int. Ed. 1998, 37, 489 E. A. Merritt, B. Olofsson, Angew. Chem. 2009, 121, 9214 P. Eisenberger, S. Gischig, A. Togni, Chem. Eur. J. 2006, 12, 2579 R. Koller, K. Stanek, D. Stolz, R. Aardoom, K. Niedermann, A. Togni, Angew. Chem. 2009, 121, 4396 M. G. Moloney, J. T. Pinhey, E. G. Roche, J. Chem. Soc. Perkin Trans. 1 1989, 333 T. B. Poulsen, L. Bernardi, J. Aleman, J. Overgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 441. Angew. Chem. Int. Ed. Engl. 1990, 29, 287 A. S. Kende, P. Fludzinski, J. H. Hill, W. Swenson, J. Clardy, J. Am. Chem. Soc. 1984, 106, 3551 M. D. Bachi, N. Barner, P. J. Stang, B. L. Williamson, J. Org. Chem. 1993, 58, 7923 S. I. Miller, J. I. Dickstein, Acc. Chem. Res. 1976, 9, 358 T. de Haro, C. Nevado, J. Am. Chem. Soc. 2010, 132, 1512 Angew. Chem. Int. Ed. 2009, 48, 9346 P. Meffre, F. LeGoffic, Amino Acids 1996, 11, 313. W. Oppolzer, O. Tamura, J. Deerberg, Helv. Chim. Acta 1992, 75, 1965. P. J. Stang, A. M. Arif, C. M. Crittell, Angew. Chem. 1990, 102, 307 M. Ochiai, T. Ito, Y. Takaoka, Y. Masaki, M. Kunishima, S. Tani, Y. Nagao, J. Chem. Soc. Chem. Commun. 1990, 118 J. F. Lutz, Angew. Chem. 2007, 119, 1036 B. Witulski, M. Gössmann, Chem. Commun. 1999, 1879. For reviews, see S. M. Abu Sohel, R. S. Liu, Chem. Soc. Rev. 2009, 38, 2269. M. Arisawa, R. Amemiya, M. Yamaguchi, Org. Lett. 2002, 4, 2209 e_1_2_3_50_2 e_1_2_3_4_2 e_1_2_3_16_2 e_1_2_3_2_2 e_1_2_3_18_2 e_1_2_3_39_2 e_1_2_3_33_3 e_1_2_3_56_2 e_1_2_3_8_2 e_1_2_3_12_2 e_1_2_3_33_2 e_1_2_3_58_2 e_1_2_3_6_2 e_1_2_3_14_2 e_1_2_3_35_2 e_1_2_3_52_2 e_1_2_3_50_3 e_1_2_3_54_2 e_1_2_3_10_2 e_1_2_3_31_2 e_1_2_3_60_2 e_1_2_3_26_2 e_1_2_3_49_2 e_1_2_3_28_2 e_1_2_3_28_3 e_1_2_3_22_2 e_1_2_3_45_2 e_1_2_3_24_2 e_1_2_3_47_2 e_1_2_3_66_2 e_1_2_3_41_2 e_1_2_3_64_2 e_1_2_3_20_2 e_1_2_3_43_2 e_1_2_3_62_2 Diederich F. (e_1_2_3_1_2) 2005 e_1_2_3_19_2 Ochiai M. (e_1_2_3_37_2) 1999 e_1_2_3_5_2 e_1_2_3_15_2 e_1_2_3_38_2 e_1_2_3_3_2 e_1_2_3_17_2 e_1_2_3_59_2 e_1_2_3_9_2 e_1_2_3_11_2 e_1_2_3_34_2 e_1_2_3_55_2 e_1_2_3_13_2 e_1_2_3_36_2 e_1_2_3_5_3 e_1_2_3_57_2 e_1_2_3_51_3 e_1_2_3_30_2 e_1_2_3_51_2 e_1_2_3_32_2 e_1_2_3_53_2 e_1_2_3_61_2 e_1_2_3_27_2 e_1_2_3_48_2 e_1_2_3_29_2 e_1_2_3_44_3 e_1_2_3_23_2 e_1_2_3_44_2 e_1_2_3_46_3 Brandsma L. (e_1_2_3_7_2) 2003 e_1_2_3_25_2 e_1_2_3_46_2 e_1_2_3_67_2 e_1_2_3_40_3 e_1_2_3_40_2 e_1_2_3_65_2 e_1_2_3_21_2 e_1_2_3_42_2 e_1_2_3_63_2 Sharpless, WD (WOS:000233334400024) 2005; 82 Alonso, F (WOS:000221968600009) 2004; 104 Sun, JW (WOS:000239278600046) 2006; 128 MOLONEY, MG (WOS:A1989T390400019) 1989 STOLZ D (WOS:000281539500016.53) 2009; 121 Chinchilla, R (WOS:000244895800008) 2007; 107 Kieltsch, I (WOS:000243855500019) 2007; 46 Merritt, EA (WOS:000272276800005) 2009; 48 STANG PJ (WOS:000281539500016.50) 1990; 102 Wei, Y (WOS:000275117900016) 2010; 132 Poulsen, TB (WOS:000243381200043) 2007; 129 Feldman, KS (WOS:000185899400020) 2003 KENDE AS (WOS:000281539500016.27) 1979; 20 KITAMURA, T (WOS:A1995QG74300027) 1995; 36 Dudnik, AS (WOS:000276008000003) 2010; 49 BACHI, MD (WOS:A1993MQ57300046) 1993; 58 NAMBU, Y (WOS:A1982NZ83300008) 1982; 47 Lutz, JF (WOS:000244195200006) 2007; 46 MILLER, SI (WOS:A1976CG34800003) 1976; 9 KENDE, AS (WOS:A1982NS51300012) 1982; 23 OPPOLZER, W (WOS:A1992JQ93700021) 1992; 75 WIRTH T (WOS:000281539500016.57) 2003; 224 Jin, CY (WOS:000246190800012) 2007; 9 Ciochina, R (WOS:000186728600023) 2003; 5 BRANDSMA L (WOS:000281539500016.8) 2003 KENDE, AS (WOS:A1984SV60800025) 1984; 106 de Haro, T (WOS:000275084900034) 2010; 132 LUTZ JF (WOS:000281539500016.33) 2007; 119 Diederich, F (WOS:000298079200001) 2005 Arisawa, M (WOS:000176354700024) 2002; 4 Eisenberger, P (WOS:000236257800020) 2006; 12 Brand, JP (WOS:000272500900030) 2009; 48 Koller, R (WOS:000267040000012) 2009; 48 Ochiai, M (CCC:000083398500012) 1999 BERINGER, FM (WOS:A19656535400054) 1965; 30 Kitamura, T (WOS:A1996VK71300031) 1996; 69 BACHI, MD (WOS:A1991FP85300025) 1991; 56 Trost, BM (WOS:000266384000002) 2009; 351 COLSON, PJ (WOS:A1993MD98500016) 1993; 58 Nishimura, Y (WOS:000235647300035) 2006; 47 Witulski, B (WOS:000082585000050) 1999 Jimenez-Nunez, E (WOS:000243443600002) 2007 KIELTSCH I (WOS:000281539500016.28) 2007; 119 Dumez, E (WOS:000072236700017) 1998 CASARA P (WOS:000281539500016.10) 1978; 19 SAUVETRE, R (WOS:A1982PJ42700010) 1982; 23 BRAND JP (WOS:000281539500016.9) 2009; 121 Keck, GE (WOS:000082710200003) 1999; 55 MERRITT EA (WOS:000281539500016.36) 2009; 121 WITULSKI B (WOS:000281539500016.58) 1998; 110 STANG, PJ (WOS:A1990DA90700013) 1990; 29 Zhdankin, VV (WOS:000261723400011) 2008; 108 Meffre, P (WOS:A1996VW77400006) 1996; 11 Nicolai, S (WOS:000273428800046) 2010; 12 Parkinson, CJ (WOS:A1997XC27900004) 1997 Meffre, P (WOS:A1996VC81800005) 1996; 52 Abu Sohel, SM (WOS:000268184600010) 2009; 38 Zhdankin, VV (WOS:000075549100002) 1998; 54 DUDNIK AS (WOS:000281539500016.17) 2010; 122 OCHIAI, M (WOS:A1990CN47600014) 1990 Witulski, B (WOS:000072421500016) 1998; 37 HASHIMOTO, SI (WOS:A1990DV32000020) 1990 |
| References_xml | – reference: B. Witulski, T. Stengel, Angew. Chem. 1998, 110, 495; – reference: E. A. Merritt, B. Olofsson, Angew. Chem. 2009, 121, 9214; – reference: J. F. Lutz, Angew. Chem. 2007, 119, 1036; – reference: Angew. Chem. Int. Ed. Engl. 1990, 29, 287; – reference: I. Kieltsch, P. Eisenberger, A. Togni, Angew. Chem. 2007, 119, 768; – reference: Angew. Chem. Int. Ed. 2007, 46, 754; – reference: Angew. Chem. Int. Ed. 2009, 48, 9346; – reference: P. Meffre, L. Gauzy, E. Branquet, P. Durand, F. LeGoffic, Tetrahedron 1996, 52, 11215; – reference: Y. Nambu, M. Kijima, T. Endo, M. Okawara, J. Org. Chem. 1982, 47, 3066. – reference: L. Brandsma, Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques (Best Synthetic Methods Series), Academic Press, New York, 2003. – reference: C. J. Parkinson, T. W. Hambley, J. T. Pinhey, J. Chem. Soc. Perkin Trans. 1 1997, 1465; – reference: M. Arisawa, R. Amemiya, M. Yamaguchi, Org. Lett. 2002, 4, 2209; – reference: A. S. Kende, M. Benechie, D. P. Curran, P. Fludzinski, W. Swenson, J. Clardy, Tetrahedron Lett. 1979, 20, 4513; – reference: S. Nicolai, S. Erard, D. Fernández González, J. Waser, Org. Lett. 2010, 12, 384. – reference: T. de Haro, C. Nevado, J. Am. Chem. Soc. 2010, 132, 1512; – reference: M. D. Bachi, N. Barner, C. M. Crittell, P. J. Stang, B. L. Williamson, J. Org. Chem. 1991, 56, 3912; – reference: A. S. Kende, P. Fludzinski, Tetrahedron Lett. 1982, 23, 2373; – reference: C. Y. Jin, J. P. Burgess, J. A. Kepler, C. E. Cook, Org. Lett. 2007, 9, 1887. – reference: P. J. Colson, L. S. Hegedus, J. Org. Chem. 1993, 58, 5918; – reference: F. M. Beringer, S. A. Galton, J. Org. Chem. 1965, 30, 1930; – reference: T. Kitamura, K. Nagata, H. Taniguchi, Tetrahedron Lett. 1995, 36, 1081; – reference: F. Diederich, P. J. Stang, R. R. Tykwinski, Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH, Weinheim, 2005. – reference: P. J. Stang, A. M. Arif, C. M. Crittell, Angew. Chem. 1990, 102, 307; – reference: A. S. Kende, P. Fludzinski, J. H. Hill, W. Swenson, J. Clardy, J. Am. Chem. Soc. 1984, 106, 3551; – reference: P. Eisenberger, S. Gischig, A. Togni, Chem. Eur. J. 2006, 12, 2579; – reference: Angew. Chem. Int. Ed. 1998, 37, 489; – reference: R. Chinchilla, C. Najera, Chem. Rev. 2007, 107, 874. – reference: S. I. Hashimoto, Y. Miyazaki, T. Shinoda, S. Ikegami, J. Chem. Soc. Chem. Commun. 1990, 1100; – reference: P. Meffre, F. LeGoffic, Amino Acids 1996, 11, 313. – reference: W. Oppolzer, O. Tamura, J. Deerberg, Helv. Chim. Acta 1992, 75, 1965. – reference: F. Alonso, I. P. Beletskaya, M. Yus, Chem. Rev. 2004, 104, 3079; – reference: R. Koller, K. Stanek, D. Stolz, R. Aardoom, K. Niedermann, A. Togni, Angew. Chem. 2009, 121, 4396; – reference: J. W. Sun, M. P. Conley, L. M. Zhang, S. A. Kozmin, J. Am. Chem. Soc. 2006, 128, 9705; – reference: B. Witulski, M. Gössmann, Chem. Commun. 1999, 1879. For reviews, see: – reference: G. E. Keck, T. T. Wager, S. F. McHardy, Tetrahedron 1999, 55, 11755. – reference: Y. Nishimura, R. Amemiya, M. Yamaguchi, Tetrahedron Lett. 2006, 47, 1839; – reference: Angew. Chem. Int. Ed. 2009, 48, 4332. – reference: R. Ciochina, R. B. Grossman, Org. Lett. 2003, 5, 4619. – reference: Angew. Chem. Int. Ed. 2010, 49, 2096, and references therein. – reference: Y. Wei, H. Q. Zhao, J. Kan, W. P. Su, M. C. Hong, J. Am. Chem. Soc. 2010, 132, 2522; – reference: S. M. Abu Sohel, R. S. Liu, Chem. Soc. Rev. 2009, 38, 2269. – reference: V. V. Zhdankin, P. J. Stang, Tetrahedron 1998, 54, 10927; – reference: E. Dumez, J. P. Dulcere, Chem. Commun. 1998, 479; – reference: R. Sauvêtre, J. F. Normant, Tetrahedron Lett. 1982, 23, 4325; – reference: S. I. Miller, J. I. Dickstein, Acc. Chem. Res. 1976, 9, 358; – reference: M. Ochiai, T. Ito, Y. Takaoka, Y. Masaki, M. Kunishima, S. Tani, Y. Nagao, J. Chem. Soc. Chem. Commun. 1990, 118; – reference: T. Wirth, M. Ochiai, V. V. Zhdankin, G. F. Koser, H. Tohma, Y. Kita, Hypervalent Iodine Chemistry: Modern Developments in Organic Synthesis, Vol. 224, Springer, Berlin, 2003; – reference: W. D. Sharpless, P. Wu, T. V. Hansen, J. G. Lindberg, J. Chem. Educ. 2005, 82, 1833. No attempt was made to optimize the reaction conditions. – reference: P. Casara, B. W. Metcalf, Tetrahedron Lett. 1978, 19, 1581; – reference: M. G. Moloney, J. T. Pinhey, E. G. Roche, J. Chem. Soc. Perkin Trans. 1 1989, 333; – reference: T. B. Poulsen, L. Bernardi, J. Aleman, J. Overgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2007, 129, 441. – reference: K. S. Feldman, ARKIVOC 2003, 179; – reference: Angew. Chem. Int. Ed. 2009, 48, 9052. – reference: J. P. Brand, J. Charpentier, J. Waser, Angew. Chem. 2009, 121, 9510; – reference: B. M. Trost, A. H. Weiss, Adv. Synth. Catal. 2009, 351, 963. – reference: V. V. Zhdankin, P. J. Stang, Chem. Rev. 2008, 108, 5299; – reference: T. Kitamura, T. Fukuoka, L. Zheng, T. Fujimoto, H. Taniguchi, Y. Fujiwara, Bull. Chem. Soc. Jpn. 1996, 69, 2649; – reference: Angew. Chem. Int. Ed. 2007, 46, 1018; – reference: E. Jimenez-Nunez, A. M. Echavarren, Chem. Commun. 2007, 333; – reference: A. S. Dudnik, V. Gevorgyan, Angew. Chem. 2010, 122, 2140; – reference: M. D. Bachi, N. Barner, P. J. Stang, B. L. Williamson, J. Org. Chem. 1993, 58, 7923; – ident: e_1_2_3_49_2 doi: 10.1002/chem.200501052 – ident: e_1_2_3_46_2 doi: 10.1002/ange.200905419 – ident: e_1_2_3_28_2 doi: 10.1002/ange.19901020317 – ident: e_1_2_3_36_2 doi: 10.1021/cr800332c – ident: e_1_2_3_19_2 doi: 10.1021/ja067289q – ident: e_1_2_3_24_2 doi: 10.1021/ol0357907 – ident: e_1_2_3_25_2 – ident: e_1_2_3_30_2 doi: 10.1021/jo00079a046 – ident: e_1_2_3_41_2 – start-page: 359 volume-title: Chemistry of Hypervalent Compounds year: 1999 ident: e_1_2_3_37_2 – ident: e_1_2_3_10_2 – ident: e_1_2_3_50_3 doi: 10.1002/anie.200603497 – ident: e_1_2_3_2_2 – ident: e_1_2_3_44_2 doi: 10.1002/ange.200906755 – ident: e_1_2_3_15_2 doi: 10.1016/S0040-4039(00)85591-4 – ident: e_1_2_3_6_2 doi: 10.1039/b807499m – ident: e_1_2_3_55_2 doi: 10.1021/jo00137a008 – ident: e_1_2_3_54_2 doi: 10.1021/ol070447d – ident: e_1_2_3_17_2 doi: 10.1016/j.tetlet.2005.12.133 – ident: e_1_2_3_50_2 doi: 10.1002/ange.200603497 – ident: e_1_2_3_20_2 – ident: e_1_2_3_8_2 doi: 10.1002/adsc.200800776 – ident: e_1_2_3_39_2 doi: 10.3998/ark.5550190.0004.620 – ident: e_1_2_3_4_2 doi: 10.1039/B612008C – ident: e_1_2_3_46_3 doi: 10.1002/anie.200905419 – ident: e_1_2_3_48_2 – ident: e_1_2_3_53_2 doi: 10.1021/ed082p1833 – ident: e_1_2_3_42_2 doi: 10.1021/ja909726h – ident: e_1_2_3_51_3 doi: 10.1002/anie.200900974 – ident: e_1_2_3_62_2 doi: 10.1021/jo00074a016 – ident: e_1_2_3_38_2 doi: 10.1007/3-540-46114-0 – ident: e_1_2_3_22_2 doi: 10.1039/a608582b – ident: e_1_2_3_45_2 – ident: e_1_2_3_61_2 doi: 10.1016/S0040-4039(01)94610-6 – ident: e_1_2_3_9_2 doi: 10.1021/cr050992x – ident: e_1_2_3_34_2 doi: 10.1039/a905898b – ident: e_1_2_3_63_2 doi: 10.1016/0040-4020(96)00630-8 – ident: e_1_2_3_67_2 – ident: e_1_2_3_31_2 doi: 10.1016/0040-4039(94)02459-O – ident: e_1_2_3_64_2 doi: 10.1007/BF00807939 – ident: e_1_2_3_11_2 doi: 10.1021/ar50106a003 – ident: e_1_2_3_51_2 doi: 10.1002/ange.200900974 – ident: e_1_2_3_58_2 doi: 10.1039/a707840d – ident: e_1_2_3_13_2 doi: 10.1016/S0040-4039(00)87345-1 – volume-title: Synthesis of Acetylenes, Allenes and Cumulenes: Methods and Techniques (Best Synthetic Methods Series) year: 2003 ident: e_1_2_3_7_2 – ident: e_1_2_3_35_2 doi: 10.1016/S0040-4020(98)00410-4 – ident: e_1_2_3_16_2 doi: 10.1021/ol026050l – ident: e_1_2_3_23_2 doi: 10.1039/C39900001100 – ident: e_1_2_3_52_2 – ident: e_1_2_3_60_2 – ident: e_1_2_3_29_2 doi: 10.1021/jo00012a025 – ident: e_1_2_3_66_2 – ident: e_1_2_3_33_2 doi: 10.1002/(SICI)1521-3757(19980216)110:4<495::AID-ANGE495>3.0.CO;2-W – ident: e_1_2_3_57_2 – ident: e_1_2_3_21_2 doi: 10.1039/P19890000333 – ident: e_1_2_3_33_3 doi: 10.1002/(SICI)1521-3773(19980302)37:4<489::AID-ANIE489>3.0.CO;2-N – ident: e_1_2_3_47_2 doi: 10.1021/ol9027286 – ident: e_1_2_3_40_3 doi: 10.1002/anie.200904689 – ident: e_1_2_3_59_2 doi: 10.1016/S0040-4020(99)00486-X – ident: e_1_2_3_40_2 doi: 10.1002/ange.200904689 – ident: e_1_2_3_65_2 – ident: e_1_2_3_5_3 doi: 10.1002/anie.200604050 – ident: e_1_2_3_18_2 doi: 10.1021/ja063384n – volume-title: Acetylene Chemistry: Chemistry, Biology and Material Science year: 2005 ident: e_1_2_3_1_2 – ident: e_1_2_3_43_2 doi: 10.1021/ja910461e – ident: e_1_2_3_27_2 doi: 10.1039/c39900000118 – ident: e_1_2_3_3_2 doi: 10.1021/cr0201068 – ident: e_1_2_3_44_3 doi: 10.1002/anie.200906755 – ident: e_1_2_3_28_3 doi: 10.1002/anie.199002871 – ident: e_1_2_3_26_2 doi: 10.1021/jo01017a053 – ident: e_1_2_3_12_2 doi: 10.1016/S0040-4039(01)86636-3 – ident: e_1_2_3_32_2 doi: 10.1246/bcsj.69.2649 – ident: e_1_2_3_56_2 doi: 10.1002/hlca.19920750622 – ident: e_1_2_3_5_2 doi: 10.1002/ange.200604050 – ident: e_1_2_3_14_2 doi: 10.1021/ja00324a025 – volume: 9 start-page: 1887 year: 2007 ident: WOS:000246190800012 article-title: Copper-catalyzed cyclization of steroidal acylaminoacetylenes: Syntheses of novel 11 beta-aryl-17,17-spiro[(4 ' H,5 '-methylene)oxazol]-substituted steroids publication-title: ORGANIC LETTERS doi: 10.1021/ol070447d – volume: 128 start-page: 9705 year: 2006 ident: WOS:000239278600046 article-title: Au- and Pt-catalyzed cycloisomerizations of 1,5-enynes to cyclohexadienes with a broad alkyne scope publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja063384n – volume: 36 start-page: 1081 year: 1995 ident: WOS:A1995QG74300027 article-title: A NOVEL HYPERVALENT IODINE REAGENT PREPARED FROM O-IODOSYLBENZOIC ACID AND TRIFLUOROMETHANESULFONIC ACID - PREPARATION AND REACTIONS OF ALKYNYL(O-CARBOXYPHENYL)IODONIUM TRIFLATES publication-title: TETRAHEDRON LETTERS – volume: 48 start-page: 9052 year: 2009 ident: WOS:000272276800005 article-title: Diaryliodonium Salts: A Journey from Obscurity to Fame publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200904689 – volume: 20 start-page: 4513 year: 1979 ident: WOS:000281539500016.27 publication-title: TETRAHEDRON LETT – volume: 48 start-page: 4332 year: 2009 ident: WOS:000267040000012 article-title: Zinc-Mediated Formation of Trifluoromethyl Ethers from Alcohols and Hypervalent Iodine Trifluoromethylation Reagents publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200900974 – year: 2003 ident: WOS:000281539500016.8 publication-title: SYNTHESIS ACETYLENES – volume: 69 start-page: 2649 year: 1996 ident: WOS:A1996VK71300031 article-title: Reaction of alkynyl(phenyl)(p-phenylene)bisiodonium ditriflates with nucleophiles. High reactivity of the alkynyl component publication-title: BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN – volume: 12 start-page: 2579 year: 2006 ident: WOS:000236257800020 article-title: Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200501052 – volume: 119 start-page: 768 year: 2007 ident: WOS:000281539500016.28 publication-title: ANGEW CHEM – volume: 46 start-page: 754 year: 2007 ident: WOS:000243855500019 article-title: Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200603497 – volume: 119 start-page: 1036 year: 2007 ident: WOS:000281539500016.33 publication-title: ANGEW CHEM – volume: 102 start-page: 307 year: 1990 ident: WOS:000281539500016.50 publication-title: ANGEW CHEM – volume: 121 start-page: 9214 year: 2009 ident: WOS:000281539500016.36 publication-title: ANGEW CHEM – start-page: 359 year: 1999 ident: CCC:000083398500012 article-title: Organic synthesis using hypervalent organoiodanes publication-title: CHEMISTRY OF HYPERVALENT COMPOUNDS – volume: 5 start-page: 4619 year: 2003 ident: WOS:000186728600023 article-title: A new synthetic approach to the polycyclic polyprenylated acylphloroglucinols publication-title: ORGANIC LETTERS doi: 10.1021/ol0357907 – volume: 82 start-page: 1833 year: 2005 ident: WOS:000233334400024 article-title: Just click it: Undergraduate procedures for the copper(I)-catalyzed formation of 1,2,3-triazoles from azides and terminal acetylenes publication-title: JOURNAL OF CHEMICAL EDUCATION – volume: 9 start-page: 358 year: 1976 ident: WOS:A1976CG34800003 article-title: NUCLEOPHILIC-SUBSTITUTION AT ACETYLENIC CARBON - LAST HOLDOUT publication-title: ACCOUNTS OF CHEMICAL RESEARCH – volume: 52 start-page: 11215 year: 1996 ident: WOS:A1996VC81800005 article-title: Synthesis of optically active beta,gamma-alkynylglycine derivatives publication-title: TETRAHEDRON – volume: 47 start-page: 3066 year: 1982 ident: WOS:A1982NZ83300008 article-title: REDUCTIVE CLEAVAGE OF HYDROXYLAMINE DERIVATIVES BY DIHYDROLIPOIC ACID-IRON(II) publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 12 start-page: 384 year: 2010 ident: WOS:000273428800046 article-title: Pd-Catalyzed Intramolecular Oxyalkynylation of Alkenes with Hypervalent Iodine publication-title: ORGANIC LETTERS doi: 10.1021/ol9027286 – volume: 49 start-page: 2096 year: 2010 ident: WOS:000276008000003 article-title: Formal Inverse Sonogashira Reaction: Direct Alkynylation of Arenes and Heterocycles with Alkynyl Halides publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200906755 – volume: 30 start-page: 1930 year: 1965 ident: WOS:A19656535400054 article-title: ACETYLENIC AND ETHYLENIC IODONIUM SALTS AND THEIR REACTIONS WITH A CARBANION publication-title: JOURNAL OF ORGANIC CHEMISTRY – start-page: 1879 year: 1999 ident: WOS:000082585000050 article-title: Stereospecific synthesis of chiral N-(ethynyl)allylglycines and their use in highly stereoselective intramolecular Pauson-Khand reactions publication-title: CHEMICAL COMMUNICATIONS – volume: 37 start-page: 489 year: 1998 ident: WOS:000072421500016 article-title: N-functionalized 1-alkynylamides: New building blocks for transition metal mediated inter- and intramolecular [2+2+1] cycloadditions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION – volume: 122 start-page: 2140 year: 2010 ident: WOS:000281539500016.17 publication-title: ANGEW CHEM – volume: 47 start-page: 1839 year: 2006 ident: WOS:000235647300035 article-title: alpha-Ethynylation reaction of ketones using catalytic amounts of trialkylgallium base publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2005.12.133 – volume: 38 start-page: 2269 year: 2009 ident: WOS:000268184600010 article-title: Carbocyclisation of alkynes with external nucleophiles catalysed by gold, platinum and other electrophilic metals publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b807499m – volume: 55 start-page: 11755 year: 1999 ident: WOS:000082710200003 article-title: Reductive cleavage of N-O bonds in hydroxylamines and hydroxamic acid derivatives using samarium diiodide publication-title: TETRAHEDRON – volume: 75 start-page: 1965 year: 1992 ident: WOS:A1992JQ93700021 article-title: ASYMMETRIC-SYNTHESIS OF ALPHA-AMINO-ACIDS AND ALPHA-N-HYDROXYAMINO ACIDS FROM N-ACYLBORNANE-10,2-SULTAMS - 1-CHLORO-1-NITROSOCYCLOHEXANE AS A PRACTICAL [NH2+] EQUIVALENT publication-title: HELVETICA CHIMICA ACTA – start-page: 333 year: 2007 ident: WOS:000243443600002 article-title: Molecular diversity through gold catalysis with alkynes publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b612008c – volume: 56 start-page: 3912 year: 1991 ident: WOS:A1991FP85300025 article-title: SYNTHESIS OF ALKYNYL(PHENYL)IODONIUM TRIFLATES AND THEIR REACTION WITH DIETHYL 2-AMINOMALONATE publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 351 start-page: 963 year: 2009 ident: WOS:000266384000002 article-title: The Enantioselective Addition of Alkyne Nucleophiles to Carbonyl Groups publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.200800776 – volume: 11 start-page: 313 year: 1996 ident: WOS:A1996VW77400006 article-title: beta,gamma-Alkynyl alpha-amino acids: A synthetic challenge publication-title: AMINO ACIDS – volume: 58 start-page: 7923 year: 1993 ident: WOS:A1993MQ57300046 article-title: SYNTHESIS OF HIGHLY FUNCTIONALIZED BETA-LACTAMS - ALKYNYLATION OF 2-OXOAZETIDIN-1-YL MALONATES publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 132 start-page: 2522 year: 2010 ident: WOS:000275117900016 article-title: Copper-Catalyzed Direct Alkynylation of Electron-Deficient Polyfluoroarenes with Terminal Alkynes Using O-2 as an Oxidant publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja910461e – start-page: 333 year: 1989 ident: WOS:A1989T390400019 article-title: THE ALPHA-ALK-1-YNYLATION OF BETA-DICARBONYL COMPOUNDS AND NITRONATE SALTS BY ALK-1-YNYL-LEAD TRIACETATES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 – volume: 132 start-page: 1512 year: 2010 ident: WOS:000275084900034 article-title: Gold-Catalyzed Ethynylation of Arenes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja909726h – start-page: 479 year: 1998 ident: WOS:000072236700017 article-title: Synthesis and reactivity of alpha-allenylhydroxylamines: a new efficient access to 3,6-dihydro-1,2-oxazines publication-title: CHEMICAL COMMUNICATIONS – start-page: 1100 year: 1990 ident: WOS:A1990DV32000020 article-title: A VERSATILE AND CONVENIENT METHOD FOR THE PREPARATION OF ALPHA-(Z)-1-ALKENYL KETONES FROM BETA-KETO BENZYL-ESTERS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – volume: 224 year: 2003 ident: WOS:000281539500016.57 publication-title: HYPERVALENT IODINE C – volume: 121 start-page: 9510 year: 2009 ident: WOS:000281539500016.9 publication-title: ANGEW CHEM – volume: 129 start-page: 441 year: 2007 ident: WOS:000243381200043 article-title: Organocatalytic asymmetric direct alpha-alkynylation of cyclic beta-ketoesters publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja067289q – start-page: 118 year: 1990 ident: WOS:A1990CN47600014 article-title: SYNTHESIS OF ETHYNYL(PHENYL)IODONIUM TETRAFLUOROBORATE - A NEW REAGENT FOR ETHYNYLATION OF 1,3-DICARBONYL COMPOUNDS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – volume: 23 start-page: 4325 year: 1982 ident: WOS:A1982PJ42700010 article-title: A NEW PREPARATION OF FLUOROACETYLENE - ITS REACTION WITH ORGANOMETALLICS - SYNTHESIS OF VARIOUS ALKYNES AND ENYNES publication-title: TETRAHEDRON LETTERS – volume: 23 start-page: 2373 year: 1982 ident: WOS:A1982NS51300012 article-title: CHLOROACETYLENES AS MICHAEL ACCEPTORS .2. DIRECT ETHYNYLATION AND VINYLATION OF TERTIARY ENOLATES publication-title: TETRAHEDRON LETTERS – volume: 110 start-page: 495 year: 1998 ident: WOS:000281539500016.58 publication-title: ANGEW CHEM – volume: 4 start-page: 2209 year: 2002 ident: WOS:000176354700024 article-title: One-step ethynylation of silyl enol ether with chlorosilylethyne publication-title: ORGANIC LETTERS doi: 10.1021/ol026050l – volume: 19 start-page: 1581 year: 1978 ident: WOS:000281539500016.10 publication-title: TETRAHEDRON LETT – start-page: 179 year: 2003 ident: WOS:000185899400020 article-title: Application of alkynyliodonium salts to natural products synthesis: A mini-review of recent work at Penn State publication-title: ARKIVOC doi: 10.3998/ark.5550190.0004.620 – volume: 48 start-page: 9346 year: 2009 ident: WOS:000272500900030 article-title: Direct Alkynylation of Indole and Pyrrole Heterocycles publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200905419 – volume: 58 start-page: 5918 year: 1993 ident: WOS:A1993MD98500016 article-title: ASYMMETRIC-SYNTHESIS OF ALPHA-ALKYL-ALPHA-AMINO ACIDS FROM CHROMIUM CARBENE-COMPLEX-DERIVED BETA-LACTAMS publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 54 start-page: 10927 year: 1998 ident: WOS:000075549100002 article-title: Alkynyliodonium salts in organic synthesis publication-title: TETRAHEDRON – volume: 106 start-page: 3551 year: 1984 ident: WOS:A1984SV60800025 article-title: CHLOROACETYLENES AS MICHAEL ACCEPTORS .3. MECHANISM AND SYNTHETIC UTILITY OF ENOLATE REACTIONS WITH HALOGENATED OLEFINS AND CHLOROACETYLENES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 107 start-page: 874 year: 2007 ident: WOS:000244895800008 article-title: The sonogashira reaction: A booming methodology in synthetic organic chemistry publication-title: CHEMICAL REVIEWS doi: 10.1021/cr050992x – start-page: V year: 2005 ident: WOS:000298079200001 article-title: Acetylene Chemistry Chemistry, Biology and Material Science Preface publication-title: ACETYLENE CHEMISTRY: CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE – volume: 104 start-page: 3079 year: 2004 ident: WOS:000221968600009 article-title: Transition-metal-catalyzed addition of heteroatom-hydrogen bonds to alkynes publication-title: CHEMICAL REVIEWS doi: 10.1021/cr0201068 – volume: 29 start-page: 287 year: 1990 ident: WOS:A1990DA90700013 article-title: ETHYNYL(PHENYL)IODONIUM TRIFLATE, [HC=CIPH][OSO2CF3] - PREPARATION, SPECTRAL PROPERTIES, MECHANISM OF FORMATION AND X-RAY MOLECULAR-STRUCTURE publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH – volume: 108 start-page: 5299 year: 2008 ident: WOS:000261723400011 article-title: Chemistry of Polyvalent Iodine publication-title: CHEMICAL REVIEWS doi: 10.1021/cr800332c – start-page: 1465 year: 1997 ident: WOS:A1997XC27900004 article-title: The in situ generation of alk-1-ynyllead triacetates from terminal acetylenes by zinc-lead exchange and crystal structure of 2,4,7,9,13-pentamethyl-9-phenylethynyl-7,10-ethenospiro[5.5]undeca-1,4-diene-3,8-dione publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 – volume: 46 start-page: 1018 year: 2007 ident: WOS:000244195200006 article-title: 1,3-dipolar cycloadditions of azides and alkynes: A universal ligation tool in polymer and materials science publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200604050 – volume: 121 start-page: 4396 year: 2009 ident: WOS:000281539500016.53 publication-title: ANGEW CHEM |
| SSID | ssj0009633 |
| Score | 2.3465385 |
| Source | Web of Science |
| SourceID | proquest pubmed webofscience crossref istex |
| SourceType | Aggregation Database Index Database Enrichment Source Publisher |
| StartPage | 9457 |
| SubjectTerms | alkynylation Chemistry Chemistry, Multidisciplinary Esters hypervalent compounds iodine Physical Sciences quaternary carbon atoms Science & Technology umpolung |
| Title | Ethynyl-1,2-benziodoxol-3(1 H)-one (EBX): An Exceptional Reagent for the Ethynylation of Keto, Cyano, and Nitro Esters |
| URI | https://api.istex.fr/ark:/67375/WNG-DH2FH6G1-W/fulltext.pdf http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000281539500016 https://www.ncbi.nlm.nih.gov/pubmed/20645361 https://www.proquest.com/docview/1767334465 https://www.proquest.com/docview/749025010 |
| Volume | 16 |
| WOS | 000281539500016 |
| WOSCitedRecordID | wos000281539500016 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| journalDatabaseRights | – providerCode: PRVWIB databaseName: Wiley Online Library Full Collection 2020 customDbUrl: eissn: 1521-3765 dateEnd: 99991231 omitProxy: false ssIdentifier: ssj0009633 issn: 0947-6539 databaseCode: DRFUL dateStart: 19980101 isFulltext: true titleUrlDefault: https://onlinelibrary.wiley.com providerName: Wiley-Blackwell |
| link | http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwtV1bb9MwFLa6FgleEHcCY_LDNDatFrk1TnjburQVVAWhjvYtSlIHVZSktOnU9a_zwvElWQoDlQdeojaxYsfns8_Fx58ROox0gzHHsgiLHIfY3sQhLlhHJAKHmSU0iVtih9znPh0M3PHY-1ir_Sj2wlzNaJq667U3_6-ihnsgbL519h_EXb4UbsBvEDpcQexw3UnwPnR9ej0jMEW1TRKxdDMF13OdzYjFSZl64PuTTJqW_vkY_qnYoL9WGS6Cbj_8IlibVA6iemdpXr5nuQyxXofi6G6xBDGY5ovs1OfMC8uqzdsuzpQ7lTurtxYAis-phrS7WboBvbUpcu7TaSVqoBIxi6h_uT1tBOpYoO-dXPsXKQDntuJiUHENmVUnt13uOHtWY5k2JZxjVyo1NZObBp89W1tTvVOBtNI-cuL2bMmT_ZtGkQy1MIC-iTxAsJ6KaqrU3YMPQeey3w-G_ni4_VSaCpwCh4JraxzNvxN-5BlPDVDnv-yhhklhSNRR4-ITvOWGMxrGkKCKVF9XcI7q5pvt9mzZVA0-Paxvc5huta2EHTV8gO4rBwifSeA-RDWWPkJ3S4w8RqsSwM1f4Hts9E44dPExAPfkLT5LcQW0WIEWA2gxgBZXQYuzBHPQNrGAbBMDjLAALJaAfYIuO_6w3SPqcBASQ2_mxJjYIWgnZ9JK4thyORWazZgXgU5JvDD2nDh29AS85UnCYriaXJPpUaiHCbWdSWI9RfUUmvwcYduMXX4QXxKZlk0TFllR7DIz0cMotCJmaogU3RvEijmfH-AyCyTntxlwcQSlODT0uiw_l5wxfyx5JKRVFgsXX3mmJW0Fo0E3uOiZnZ7TNYKRhvYLcQZqcC4Dg0JRizMeagiXj0FafM0vTFm2WgbU5nkEUJ-GnkkUlHWZnKrScgwNHVZhUT4XkXfeypZwDDVk7FKsrTqIU2rkL_7e7Jfo3s3I30f1fLFir9Cd-CqfLhcHaI-O3QM1KH4CzST7Hw |
| linkProvider | Wiley-Blackwell |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=Ethynyl-1%2C2-benziodoxol-3%281H%29-one+%28EBX%29%3A+An+Exceptional+Reagent+for+the+Ethynylation+of+Keto%2C+Cyano%2C+and+Nitro+Esters&rft.jtitle=Chemistry+%3A+a+European+journal&rft.au=FernandezGonzalez%2C+Davinia&rft.au=Brand%2C+JonathanP&rft.au=Waser%2C+J%C3%A9r%C3%B4me&rft.date=2010-08-16&rft.pub=Wiley+Subscription+Services%2C+Inc&rft.issn=0947-6539&rft.eissn=1521-3765&rft.volume=16&rft.issue=31&rft.spage=9457&rft_id=info:doi/10.1002%2Fchem.201001539&rft.externalDBID=NO_FULL_TEXT&rft.externalDocID=3960478991 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0947-6539&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0947-6539&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0947-6539&client=summon |