Transition metal-free cross-dehydrogenative arylation of unactivated benzylic C-H bonds
The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or no...
Uložené v:
| Vydané v: | Chemical communications (Cambridge, England) Ročník 56; číslo 92; s. 14479 - 14482 |
|---|---|
| Hlavní autori: | , , , , , |
| Médium: | Journal Article |
| Jazyk: | English |
| Vydavateľské údaje: |
CAMBRIDGE
Royal Soc Chemistry
19.11.2020
|
| Predmet: | |
| ISSN: | 1359-7345, 1364-548X, 1364-548X |
| On-line prístup: | Zistit podrobnosti o prístupe |
| Tagy: |
Pridať tag
Žiadne tagy, Buďte prvý, kto otaguje tento záznam!
|
| Abstract | The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or non-trivial reaction set up. We report a transition metal-free cross-dehydrogenative arylation of benzylic C-H bonds using alkyl benzene derivatives and electron-rich arenes as coupling partners. The method proceeds through the in situ generation of a reactive benzyl fluoride intermediate which then reacts with the nucleophilic arene. The reaction tolerates a wide variety of functional groups including unprotected polar functionality and has been applied to the late-stage benzylation of several biologically relevant molecules. |
|---|---|
| AbstractList | The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or non-trivial reaction set up. We report a transition metal-free cross-dehydrogenative arylation of benzylic C-H bonds using alkyl benzene derivatives and electron-rich arenes as coupling partners. The method proceeds through the in situ generation of a reactive benzyl fluoride intermediate which then reacts with the nucleophilic arene. The reaction tolerates a wide variety of functional groups including unprotected polar functionality and has been applied to the late-stage benzylation of several biologically relevant molecules. The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or non-trivial reaction set up. We report a transition metal-free cross-dehydrogenative arylation of benzylic C-H bonds using alkyl benzene derivatives and electron-rich arenes as coupling partners. The method proceeds through the in situ generation of a reactive benzyl fluoride intermediate which then reacts with the nucleophilic arene. The reaction tolerates a wide variety of functional groups including unprotected polar functionality and has been applied to the late-stage benzylation of several biologically relevant molecules.The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily available starting materials. Current approaches suffer from limited substrate scope, requirement for large excesses of alkyl arene and/or non-trivial reaction set up. We report a transition metal-free cross-dehydrogenative arylation of benzylic C-H bonds using alkyl benzene derivatives and electron-rich arenes as coupling partners. The method proceeds through the in situ generation of a reactive benzyl fluoride intermediate which then reacts with the nucleophilic arene. The reaction tolerates a wide variety of functional groups including unprotected polar functionality and has been applied to the late-stage benzylation of several biologically relevant molecules. |
| Author | Bentkowska, Katarzyna Larrosa, Igor Grainger, Rachel Spencer, Andrew R. A. Panigrahi, Adyasha Lepper, Thomas J. |
| Author_xml | – sequence: 1 givenname: Andrew R. A. surname: Spencer fullname: Spencer, Andrew R. A. organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 2 givenname: Rachel orcidid: 0000-0002-3944-0201 surname: Grainger fullname: Grainger, Rachel organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 3 givenname: Adyasha surname: Panigrahi fullname: Panigrahi, Adyasha organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 4 givenname: Thomas J. orcidid: 0000-0003-4255-7651 surname: Lepper fullname: Lepper, Thomas J. organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 5 givenname: Katarzyna surname: Bentkowska fullname: Bentkowska, Katarzyna organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England – sequence: 6 givenname: Igor orcidid: 0000-0002-5391-7424 surname: Larrosa fullname: Larrosa, Igor email: igor.larrosa@manchester.ac.uk organization: Univ Manchester, Sch Nat Sci, Dept Chem, Oxford Rd, Manchester M13 9PL, Lancs, England |
| BookMark | eNqNkMtOwzAQRS1URB-w4QuyREIGP9NkiSJeUiU2RbCLXHsMrlK7xA6ofD2m5QOYzVzNnDvSnSka-eABoXNKrijh9bUhWpOSUbY-QhPKS4GlqF5Hv1rWeM6FHKNpjGuSi8rqBI05p5JwISboZdkrH11ywRcbSKrDtgcodB9ixAbed6YPb-BVcp9QqH7XqT0abDF4pfNUJTDFCvz3rnO6aPBDsQrexFN0bFUX4eyvz9Dz3e2yecCLp_vH5maBNSdlwkaXUAEBqbQgsiJ2ZQiAUSBKzaqSMUlrntfWSiWUEEYxVgsJ2ppaADVshi4Od7d9-BggpnbjooauUx7CEFsm5Lwu5xWvM1od0C9YBRu1A6-h3fZuk3O1-TeyprKsRFacNS7tkzZh8ClbL_9vZT9CC3rY |
| Cites_doi | 10.1021/jo5016757 10.1039/c1cs15083a 10.1007/s40502-019-0436-6 10.1016/j.tetlet.2017.01.035 10.1039/b003686m 10.1002/anie.201309084 10.1021/jacs.0c00169 10.1021/cr0509760 10.1021/ja402479r 10.1021/acs.orglett.7b01270 10.1021/ja410815u 10.1002/adsc.201400938 10.1021/acs.orglett.7b01188 10.1021/ol4001153 10.1016/j.jfluchem.2009.02.012 10.1021/jacs.6b05273 10.1021/jo2021373 10.1021/jo2015533 10.1016/j.bmcl.2006.03.075 10.1016/j.ejmech.2006.09.020 10.1002/anie.201406088 10.1002/anie.200806273 10.1021/jo401796g 10.1039/c4ob02418d 10.1021/acs.orglett.7b00712 10.1021/jo0510437 10.1038/s41557-018-0048-1 10.1016/bs.adomc.2017.03.002 10.1016/j.jfluchem.2014.08.018 10.1002/chem.202001905 10.1021/acs.orglett.5b02898 10.1021/acs.joc.5b01935 10.1021/ol4006757 10.1021/acs.orglett.7b01529 10.1021/jo201511d 10.1021/ol5018883 10.1039/c6qo00674d 10.1016/j.jfluchem.2016.08.003 10.3762/bjoc.9.283 10.1039/b600091f 10.1021/ja0516054 10.1021/ol503094m 10.1021/jacs.7b03781 10.1021/acscatal.6b00866 10.1021/acs.orglett.0c02238 10.1039/c8sc02758g 10.1002/chem.201603783 10.1039/c5cs00003c 10.1002/anie.201304268 10.1021/acs.orglett.9b00294 10.1002/anie.201804997 10.1021/ol400424s 10.1021/ar800164n 10.1002/anie.201603627 10.1039/c1cc15050b 10.1039/c0cc02491k 10.1021/jacs.8b05143 10.1021/ol400765a 10.3762/bjoc.14.6 10.1002/anie.200902996 10.1021/ol300627p 10.1021/jacs.7b03387 10.1039/c4cc05650g 10.1002/anie.201301097 |
| ContentType | Journal Article |
| DBID | 17B 1KM 1KN AOWDO BLEPL DTL EGQ 7X8 |
| DOI | 10.1039/d0cc06212j |
| DatabaseName | Web of Knowledge Index Chemicus Current Chemical Reactions Web of Science - Science Citation Index Expanded - 2020 Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) MEDLINE - Academic |
| DatabaseTitle | Web of Science MEDLINE - Academic |
| DatabaseTitleList | Web of Science MEDLINE - Academic |
| Database_xml | – sequence: 1 dbid: 1KM name: Index Chemicus url: https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database – sequence: 2 dbid: 7X8 name: MEDLINE - Academic url: https://search.proquest.com/medline sourceTypes: Aggregation Database |
| DeliveryMethod | no_fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1364-548X |
| EndPage | 14482 |
| ExternalDocumentID | 000591568400032 |
| GrantInformation_xml | – fundername: European Research Council; European Research Council (ERC) |
| GroupedDBID | --- -DZ -~X 0-7 0R~ 17B 1KM 1KN 29B 2WC 4.4 53G 5GY 6J9 705 70~ 7~J AAEMU AAFBY AAHBH AAIWI AAJAE AAMEH AANOJ AAWGC AAXHV AAXPP ABASK ABDVN ABEMK ABJNI ABPDG ABRYZ ABXOH ACBEA ACGFO ACGFS ACIWK ACLDK ACNCT ADMRA ADSRN AEFDR AENEX AENGV AESAV AETIL AFLYV AFOGI AFRDS AFRZK AFVBQ AGEGJ AGKEF AGRSR AHGCF AKMSF ALMA_UNASSIGNED_HOLDINGS ALUYA ANUXI APEMP ASKNT AUDPV AZFZN BLAPV BLEPL BSQNT C6K CS3 DTL DU5 EBS ECGLT EE0 EF- F5P GGIMP GNO GROUPED_WOS_WEB_OF_SCIENCE H13 HZ~ H~N IDZ IH2 J3I M4U N9A O9- P2P R56 R7B R7C R7D RAOCF RCNCU RPMJG RRA RRC RSCEA SJN SKA SKF SKH SLH TN5 TWZ UPT VH6 WH7 X7L 7X8 |
| ID | FETCH-LOGICAL-c306t-dc6e8e0e5ac40580fbd0eedae46c2862251930e5ff5a4a44da22945ecfd94e1d2 |
| IEDL.DBID | 7X8 |
| ISICitedReferencesCount | 15 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000591568400032 |
| ISSN | 1359-7345 1364-548X |
| IngestDate | Thu Jul 10 17:38:25 EDT 2025 Fri Dec 05 22:43:29 EST 2025 Mon Oct 27 23:22:14 EDT 2025 |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 92 |
| Keywords | F BONDS FUNCTIONALIZATION C(SP)-H BONDS ACTIVATION COUPLING REACTIONS LIGHT OXIDATIVE ARYLATION IRON FLUORINATION FLUORIDES |
| Language | English |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c306t-dc6e8e0e5ac40580fbd0eedae46c2862251930e5ff5a4a44da22945ecfd94e1d2 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0002-5391-7424 0000-0003-4255-7651 0000-0002-3944-0201 |
| PMID | 33150344 |
| PQID | 2457967839 |
| PQPubID | 23479 |
| PageCount | 4 |
| ParticipantIDs | proquest_miscellaneous_2457967839 webofscience_primary_000591568400032CitationCount webofscience_primary_000591568400032 |
| PublicationCentury | 2000 |
| PublicationDate | 20201119 |
| PublicationDateYYYYMMDD | 2020-11-19 |
| PublicationDate_xml | – month: 11 year: 2020 text: 20201119 day: 19 |
| PublicationDecade | 2020 |
| PublicationPlace | CAMBRIDGE |
| PublicationPlace_xml | – name: CAMBRIDGE |
| PublicationTitle | Chemical communications (Cambridge, England) |
| PublicationTitleAbbrev | CHEM COMMUN |
| PublicationYear | 2020 |
| Publisher | Royal Soc Chemistry |
| Publisher_xml | – name: Royal Soc Chemistry |
| References | Champagne, PA (WOS:000318588900036) 2013; 15 Wencel-Delord, J (WOS:000293858500016) 2011; 40 Jaiswal, AK (WOS:000398985800112) 2017; 19 Dhineshkumar, J (WOS:000315707400030) 2013; 15 Vasilopoulos, A (WOS:000562077400009) 2020; 22 Li, ZP (WOS:000229085200028) 2005; 127 Champagne, PA (WOS:000350943600018) 2015; 171 OLAH, GA (WOS:A1987H723400030) 1987; 109 Bloom, S (WOS:000326615300055) 2013; 78 Whiting, DA (WOS:000172902600001) 2001; 18 Champagne, PA (WOS:000345833100035) 2014; 53 Bloom, S (WOS:000317327900077) 2013; 15 Kainuma, M (WOS:000237763500027) 2006; 16 Varun, BV (WOS:000394397700002) 2017; 58 Hemelaere, R (WOS:000385320500001) 2016; 190 Alagiri, K (WOS:000296020200062) 2011; 47 Ratnikov, MO (WOS:000321236600047) 2013; 135 Xiang, M (WOS:000402850900059) 2017; 19 Park, H (WOS:000436103200013) 2018; 10 Vasilopoulos, A (WOS:000403631200009) 2017; 139 Su, WK (WOS:000296206400060) 2011; 76 Storr, TE (WOS:000390604600042) 2016; 22 Amaoka, Y (WOS:000318588900023) 2013; 15 Li, CJ (WOS:000263428300012) 2009; 42 Xia, JB (WOS:000342069600019) 2014; 50 Keddie, NS (WOS:000423182500001) 2018; 14 Wang, LF (WOS:000395903800008) 2017; 4 Schmidt, F (WOS:000237026100005) 2006; 35 Bloom, S (WOS:000346759900019) 2014; 16 Sasi, JM (WOS:000501024600001) 2019; 24 Sha, SC (WOS:000446920100022) 2018; 140 Muraoka, N (WOS:000231183000049) 2005; 70 Ueda, H (WOS:000340517200035) 2014; 16 Ghobrial, M (WOS:000296206400020) 2011; 76 Xie, W (WOS:000529156100036) 2020; 142 Ma, JJ (WOS:000350674400008) 2015; 13 Dryzhakov, M (WOS:000377326700033) 2016; 6 Ghobrial, M (WOS:000284229400042) 2010; 46 Vanjari, R (WOS:000364065800005) 2015; 44 Hua, AM (WOS:000402850900044) 2017; 19 Lee, E (WOS:000266953500005) 2009; 130 Alberico, D (WOS:000243381000008) 2007; 107 Girard, SA (WOS:000328714900008) 2014; 53 Li, B (WOS:000407307900002) 2017; 19 Jiang, H (WOS:000461843900040) 2019; 21 Chen, X (WOS:000267809800005) 2009; 48 Zhu, JT (WOS:000383253300049) 2016; 55 Champagne, PA (WOS:000327707700001) 2013; 9 Zhang, HJ (WOS:000365462600011) 2015; 80 Imada, Y (WOS:000443675700054) 2018; 57 Hussain, N (WOS:000333447500011) 2014; 53 Liu, W (WOS:000319742400022) 2013; 52 Houle, C (WOS:000550440800001) 2020; 26 Zhang, W (WOS:000403631200010) 2017; 139 Hayashi, R (WOS:000379794400021) 2016; 138 Guo, SB (WOS:000351224500012) 2015; 357 Simonetti, M (WOS:000414252300005) 2017; 67 Dastbaravardeh, N (WOS:000302387800070) 2012; 14 Ackermann, L (WOS:000273452200008) 2009; 48 Li, Y.-Z. (000591568400032.35) 2009; 121 Cantillo, D (WOS:000341345400079) 2014; 79 Panda, G (WOS:000245475900015) 2007; 42 Kim, BS (WOS:000366152000017) 2015; 17 Xia, JB (WOS:000327413300039) 2013; 135 Lovato, K (WOS:000450897900008) 2018; 9 Park, SJ (WOS:000299238400014) 2012; 77 |
| References_xml | – volume: 79 start-page: 8486 year: 2014 ident: WOS:000341345400079 article-title: A Continuous-Flow Protocol for Light-Induced Benzylic Fluorinations publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo5016757 – volume: 40 start-page: 4740 year: 2011 ident: WOS:000293858500016 article-title: Towards mild metal-catalyzed C-H bond activation publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c1cs15083a – volume: 24 start-page: 1 year: 2019 ident: WOS:000501024600001 article-title: Identification and characterization of miRNAs during flag leaf senescence in rice by high-throughput sequencing publication-title: PLANT PHYSIOLOGY REPORTS doi: 10.1007/s40502-019-0436-6 – volume: 109 start-page: 3708 year: 1987 ident: WOS:A1987H723400030 article-title: AROMATIC-SUBSTITUTION .53. ELECTROPHILIC NITRATION, HALOGENATION, ACYLATION, AND ALKYLATION OF ALPHA,ALPHA,ALPHA-TRIFLUOROMETHOXYBENZENE publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 58 start-page: 803 year: 2017 ident: WOS:000394397700002 article-title: Recent advancements in dehydrogenative cross coupling reactions for C-C bond formation publication-title: TETRAHEDRON LETTERS doi: 10.1016/j.tetlet.2017.01.035 – volume: 18 start-page: 583 year: 2001 ident: WOS:000172902600001 article-title: Natural phenolic compounds 1900-2000: a bird's eye view of a century's chemistry publication-title: NATURAL PRODUCT REPORTS doi: 10.1039/b003686m – volume: 53 start-page: 3693 year: 2014 ident: WOS:000333447500011 article-title: Chemo-and Regioselective C( sp3) 0-H Arylation of Unactivated Allylarenes by Deprotonative Cross-Coupling publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201309084 – volume: 142 start-page: 7487 year: 2020 ident: WOS:000529156100036 article-title: Copper-Catalyzed Direct C-H Alkylation of Polyfluoroarenes by Using Hydrocarbons as an Alkylating Source publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.0c00169 – volume: 107 start-page: 174 year: 2007 ident: WOS:000243381000008 article-title: Aryl-aryl bond formation by transition-metal-catalyzed direct arylation publication-title: CHEMICAL REVIEWS doi: 10.1021/cr0509760 – volume: 135 start-page: 9475 year: 2013 ident: WOS:000321236600047 article-title: Simple and Sustainable Iron-Catalyzed Aerobic C-H Functionalization of N,N-Dialkylanilines publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja402479r – volume: 19 start-page: 3009 year: 2017 ident: WOS:000402850900059 article-title: Exploring the Reducing Ability of Organic Dye (Acr+-Mes) for Fluorination and Oxidation of Benzylic C(sp3)-H Bonds under Visible Light Irradiation publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b01270 – volume: 135 start-page: 17494 year: 2013 ident: WOS:000327413300039 article-title: Visible Light-Promoted Metal-Free C-H Activation: Diarylketone-Catalyzed Selective Benzylic Mono- and Difluorination publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja410815u – volume: 357 start-page: 950 year: 2015 ident: WOS:000351224500012 article-title: Iron-Catalyzed Cross Dehydrogenative Coupling (CDC) of Indoles and Benzylic C-H Bonds publication-title: ADVANCED SYNTHESIS & CATALYSIS doi: 10.1002/adsc.201400938 – volume: 19 start-page: 2949 year: 2017 ident: WOS:000402850900044 article-title: Radical C-H Fluorination Using Unprotected Amino Acids as Radical Precursors publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b01188 – volume: 15 start-page: 1092 year: 2013 ident: WOS:000315707400030 article-title: A Versatile C-H Functionalization of Tetrahydroisoquinolines Catalyzed by Iodine at Aerobic Conditions publication-title: ORGANIC LETTERS doi: 10.1021/ol4001153 – volume: 130 start-page: 474 year: 2009 ident: WOS:000266953500005 article-title: On the isolation of neat allylic fluorides publication-title: JOURNAL OF FLUORINE CHEMISTRY doi: 10.1016/j.jfluchem.2009.02.012 – volume: 138 start-page: 8400 year: 2016 ident: WOS:000379794400021 article-title: The Stabilized Cation Pool Method: Metal- and Oxidant-Free Benzylic C-H/Aromatic C-H Cross-Coupling publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.6b05273 – volume: 77 start-page: 949 year: 2012 ident: WOS:000299238400014 article-title: Oxidative Arylation of Isochroman publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo2021373 – volume: 76 start-page: 9144 year: 2011 ident: WOS:000296206400060 article-title: Solvent-Free Cross-Dehydrogenative Coupling Reactions under High Speed Ball-Milling Conditions Applied to the Synthesis of Functionalized Tetrahydroisoquinolines publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo2015533 – volume: 16 start-page: 3213 year: 2006 ident: WOS:000237763500027 article-title: Diphenylmethane skeleton as a multi-template for nuclear receptor ligands: Preparation of FXR and PPAR ligands publication-title: BIOORGANIC & MEDICINAL CHEMISTRY LETTERS doi: 10.1016/j.bmcl.2006.03.075 – volume: 42 start-page: 410 year: 2007 ident: WOS:000245475900015 article-title: Effect of substituents on diarylmethanes for antitubercular activity publication-title: EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY doi: 10.1016/j.ejmech.2006.09.020 – volume: 53 start-page: 13835 year: 2014 ident: WOS:000345833100035 article-title: Friedel-Crafts Reaction of Benzyl Fluorides: Selective Activation of C-F Bonds as Enabled by Hydrogen Bonding publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201406088 – volume: 48 start-page: 5094 year: 2009 ident: WOS:000267809800005 article-title: Palladium(II)-Catalyzed C-H Activation/C-C Cross-Coupling Reactions: Versatility and Practicality publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200806273 – volume: 121 start-page: 3875 year: 2009 ident: 000591568400032.35 publication-title: Angew. Chem., Int. Ed. – volume: 78 start-page: 11082 year: 2013 ident: WOS:000326615300055 article-title: Metal-Catalyzed Benzylic Fluorination as a Synthetic Equivalent to 1,4-Conjugate Addition of Fluoride publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo401796g – volume: 13 start-page: 2890 year: 2015 ident: WOS:000350674400008 article-title: Transition-metal-free C-H oxidative activation: persulfate-promoted selective benzylic mono- and difluorination publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c4ob02418d – volume: 19 start-page: 1934 year: 2017 ident: WOS:000398985800112 article-title: Aluminum-Catalyzed Cross-Coupling of Silylalkynes with Aliphatic C-F Bonds publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b00712 – volume: 70 start-page: 6933 year: 2005 ident: WOS:000231183000049 article-title: Rapid synthesis of CDP840 with 2-pyrimidyl vinyl sulfide as a platform publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo0510437 – volume: 10 start-page: 755 year: 2018 ident: WOS:000436103200013 article-title: Controlling Pd(IV) reductive elimination pathways enables Pd(II)-catalysed enantioselective C(sp3)-H fluorination publication-title: NATURE CHEMISTRY doi: 10.1038/s41557-018-0048-1 – volume: 67 start-page: 299 year: 2017 ident: WOS:000414252300005 article-title: Biaryl Synthesis via C-H Bond Activation: Strategies and Methods publication-title: ADVANCES IN ORGANOMETALLIC CHEMISTRY, VOL 67 doi: 10.1016/bs.adomc.2017.03.002 – volume: 171 start-page: 113 year: 2015 ident: WOS:000350943600018 article-title: Revised mechanistic explanation for the alcohol-promoted amination of benzylic fluorides under highly concentrated conditions: Computational and experimental evidence on a model substrate publication-title: JOURNAL OF FLUORINE CHEMISTRY doi: 10.1016/j.jfluchem.2014.08.018 – volume: 26 start-page: 10620 year: 2020 ident: WOS:000550440800001 article-title: Thiourea-Catalyzed C-F Bond Activation: Amination of Benzylic Fluorides publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.202001905 – volume: 17 start-page: 5788 year: 2015 ident: WOS:000366152000017 article-title: Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.5b02898 – volume: 80 start-page: 11322 year: 2015 ident: WOS:000365462600011 article-title: Copper-Catalyzed Direct C2-Benzylation of Indoles with Alkylarenes publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.5b01935 – volume: 15 start-page: 2160 year: 2013 ident: WOS:000318588900023 article-title: Metal-Free Fluorination of C(sp3)-H Bonds Using a Catalytic N-Oxyl Radical publication-title: ORGANIC LETTERS doi: 10.1021/ol4006757 – volume: 19 start-page: 3950 year: 2017 ident: WOS:000407307900002 article-title: 2 Ru-Catalyzed Meta-C-H Benzylation of Arenes with Toluene Derivatives publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.7b01529 – volume: 76 start-page: 8781 year: 2011 ident: WOS:000296206400020 article-title: Direct Functionalization of (Un)protected Tetrahydroisoquinoline and Isochroman under Iron and Copper Catalysis: Two Metals, Two Mechanisms publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo201511d – volume: 16 start-page: 4194 year: 2014 ident: WOS:000340517200035 article-title: Acetic Acid Promoted Metal-Free Aerobic Carbon-Carbon Bond Forming Reactions at α-Position of Tertiary Amines publication-title: ORGANIC LETTERS doi: 10.1021/ol5018883 – volume: 4 start-page: 214 year: 2017 ident: WOS:000395903800008 article-title: The stability and reactivity of tri-, di-, and monofluoromethyl/methoxy/methylthio groups on arenes under acidic and basic conditions publication-title: ORGANIC CHEMISTRY FRONTIERS doi: 10.1039/c6qo00674d – volume: 190 start-page: 1 year: 2016 ident: WOS:000385320500001 article-title: Faster initiation in the Friedel-Crafts reaction of benzyl fluorides using trifluoroacetic acid as activator publication-title: JOURNAL OF FLUORINE CHEMISTRY doi: 10.1016/j.jfluchem.2016.08.003 – volume: 9 start-page: 2451 year: 2013 ident: WOS:000327707700001 article-title: Triol-promoted activation of C-F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl)propane publication-title: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY doi: 10.3762/bjoc.9.283 – volume: 35 start-page: 454 year: 2006 ident: WOS:000237026100005 article-title: Catalytic asymmetric approaches towards enantiomerically enriched diarylmethanols and diarylmethylamines publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/b600091f – volume: 127 start-page: 6968 year: 2005 ident: WOS:000229085200028 article-title: CuBr-catalyzed direct indolation of tetrahydroisoquinolines via cross-dehydrogenative coupling between sp3 C-H and sp2 C-H bonds publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja0516054 – volume: 16 start-page: 6338 year: 2014 ident: WOS:000346759900019 article-title: Photocatalyzed Benzylic Fluorination: Shedding "Light" on the Involvement of Electron Transfer publication-title: ORGANIC LETTERS doi: 10.1021/ol503094m – volume: 139 start-page: 7709 year: 2017 ident: WOS:000403631200010 article-title: Copper-Catalyzed Arylation of Benzylic C-H bonds with Alkylarenes as the Limiting Reagents publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b03781 – volume: 6 start-page: 3670 year: 2016 ident: WOS:000377326700033 article-title: Autocatalytic Friedel-Crafts Reactions of Tertiary Aliphatic Fluorides Initiated by B(C6F5)3•H2O publication-title: ACS CATALYSIS doi: 10.1021/acscatal.6b00866 – volume: 22 start-page: 5753 year: 2020 ident: WOS:000562077400009 article-title: Copper-Catalyzed C-H Fluorination/Functionalization Sequence Enabling Benzylic C-H Cross Coupling with Diverse Nucleophiles publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.0c02238 – volume: 9 start-page: 7992 year: 2018 ident: WOS:000450897900008 article-title: Transition metal-free direct dehydrogenative arylation of activated C(sp3)-H bonds: synthetic ambit and DFT reactivity predictions publication-title: CHEMICAL SCIENCE doi: 10.1039/c8sc02758g – volume: 22 start-page: 18169 year: 2016 ident: WOS:000390604600042 article-title: Cross-Dehydrogenative-Coupling of Alkoxybenzenes with Toluenes: Copper(II) Halide Mediated Tandem Halo/Benzylation of Arenes publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201603783 – volume: 44 start-page: 8062 year: 2015 ident: WOS:000364065800005 article-title: Utilization of methylarenes as versatile building blocks in organic synthesis publication-title: CHEMICAL SOCIETY REVIEWS doi: 10.1039/c5cs00003c – volume: 53 start-page: 74 year: 2014 ident: WOS:000328714900008 article-title: The Cross-Dehydrogenative Coupling of Csp3-H Bonds: A Versatile Strategy for C-C Bond Formations publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201304268 – volume: 21 start-page: 1735 year: 2019 ident: WOS:000461843900040 article-title: Ni(NIXANTPHOS)-Catalyzed Mono-Arylation of Toluenes with Aryl Chlorides and Bromides publication-title: ORGANIC LETTERS doi: 10.1021/acs.orglett.9b00294 – volume: 57 start-page: 12136 year: 2018 ident: WOS:000443675700054 article-title: Metal- and Reagent-Free Dehydrogenative Formal Benzyl-Aryl Cross-Coupling by Anodic Activation in 1,1,1,3,3,3-Hexafluoropropan-2-ol publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201804997 – volume: 15 start-page: 1722 year: 2013 ident: WOS:000317327900077 article-title: Iron(II)-Catalyzed Benzylic Fluorination publication-title: ORGANIC LETTERS doi: 10.1021/ol400424s – volume: 42 start-page: 335 year: 2009 ident: WOS:000263428300012 article-title: Cross-Dehydrogenative Coupling (CDC): Exploring C-C Bond Formations beyond Functional Group Transformations publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar800164n – volume: 55 start-page: 8448 year: 2016 ident: WOS:000383253300049 article-title: C-C Coupling of Benzyl Fluorides Catalyzed by an Electrophilic Phosphonium Cation publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201603627 – volume: 47 start-page: 11787 year: 2011 ident: WOS:000296020200062 article-title: An oxidative cross-dehydrogenative-coupling reaction in water using molecular oxygen as the oxidant: vanadium catalyzed indolation of tetrahydroisoquinolines publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c1cc15050b – volume: 46 start-page: 8836 year: 2010 ident: WOS:000284229400042 article-title: Facile, solvent and ligand free iron catalyzed direct functionalization of N-protected tetrahydroisoquinolines and isochroman publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c0cc02491k – volume: 140 start-page: 12415 year: 2018 ident: WOS:000446920100022 article-title: Cation-π Interactions in the Benzylic Arylation of Toluenes with Bimetallic Catalysts publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.8b05143 – volume: 15 start-page: 2210 year: 2013 ident: WOS:000318588900036 article-title: Enabling Nucleophilic Substitution Reactions of Activated Alkyl Fluorides through Hydrogen Bonding publication-title: ORGANIC LETTERS doi: 10.1021/ol400765a – volume: 14 start-page: 106 year: 2018 ident: WOS:000423182500001 article-title: Stereochemical outcomes of C-F activation reactions of benzyl fluoride publication-title: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY doi: 10.3762/bjoc.14.6 – volume: 48 start-page: 9792 year: 2009 ident: WOS:000273452200008 article-title: Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.200902996 – volume: 14 start-page: 1930 year: 2012 ident: WOS:000302387800070 article-title: Ruthenium(0)-Catalyzed sp3 C-H Bond Arylation of Benzylic Amines Using Arylboronates publication-title: ORGANIC LETTERS doi: 10.1021/ol300627p – volume: 139 start-page: 7705 year: 2017 ident: WOS:000403631200009 article-title: Feedstocks to Pharmacophores: Cu-Catalyzed Oxidative Arylation of Inexpensive Alkylarenes Enabling Direct Access to Diarylalkanes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/jacs.7b03387 – volume: 50 start-page: 11701 year: 2014 ident: WOS:000342069600019 article-title: Visible light-promoted metal-free sp3-C-H fluorination publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c4cc05650g – volume: 52 start-page: 6024 year: 2013 ident: WOS:000319742400022 article-title: Manganese-Catalyzed Oxidative Benzylic C-H Fluorination by Fluoride Ions publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201301097 |
| SSID | ssj0000158 |
| Score | 2.426152 |
| Snippet | The cross-dehydrogenative arylation of benzylic C-H bonds with arenes provides straightforward access to synthetically useful 1,1-diarylmethanes, from readily... |
| Source | Web of Science |
| SourceID | proquest webofscience |
| SourceType | Aggregation Database Enrichment Source Index Database |
| StartPage | 14479 |
| SubjectTerms | Chemistry Chemistry, Multidisciplinary Physical Sciences Science & Technology |
| Title | Transition metal-free cross-dehydrogenative arylation of unactivated benzylic C-H bonds |
| URI | http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000591568400032 https://www.proquest.com/docview/2457967839 |
| Volume | 56 |
| WOS | 000591568400032 |
| WOSCitedRecordID | wos000591568400032 |
| hasFullText | |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV3fS8MwEA7qBH3xtzh_jAh7DevatEueRIZjoA4fFPs20lyKirZz3Qbzr_eStTjBh4FvhRbaHpf7vkvuviOkCUmgFSTAlK88xoELJkQYMo1kRILs6Eg5df27zmAg4lg-lBtuRVlWWcVEF6gh13aPvOVz2zXZQTy_Gn0yOzXKnq6WIzTWSS1AKmNLujqxWJKPcvM520HEGTLzuJInDWQLPK29COP22y9q-Qf4OKDp7f73E_fITkkx6fXCJ_bJmskOyFa3mux2SJ4dQLlaLfphkH2zdGwMdYDJwLzMYZyjXzlJcKrG80W5HM1TOs1sH8QM-SnQxGRf8_dXTbusT5M8g-KIPPVuHrt9Vg5YYBozhQkDHRlhPBMqjbxNeGkCHmKmMjzSPqY6tqs1wNtpGiquOAfl-5KHRqcguWmDf0w2sjwzJ4QKqaWIQq7QrjxJPaXAREoFeKGRUyR1clnZbIh_a08lVGbyaTH8sVqdNJfNPxwt9DaGTkQG80zMRTEG-XXSXuWxbqlxbnv7J6crvP6MbPs2mbY1fvKc1FJc_-aCbOrZ5LUYN5B73943nIN9A0cA3Hw |
| linkProvider | ProQuest |
| 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=Transition+metal-free+cross-dehydrogenative+arylation+of+unactivated+benzylic+C-H+bonds&rft.jtitle=Chemical+communications+%28Cambridge%2C+England%29&rft.au=Spencer%2C+Andrew+R.+A.&rft.au=Grainger%2C+Rachel&rft.au=Panigrahi%2C+Adyasha&rft.au=Lepper%2C+Thomas+J.&rft.date=2020-11-19&rft.pub=Royal+Soc+Chemistry&rft.issn=1359-7345&rft.eissn=1364-548X&rft.volume=56&rft.issue=92&rft.spage=14479&rft.epage=14482&rft_id=info:doi/10.1039%2Fd0cc06212j&rft_id=info%3Apmid%2F33150344&rft_id=info%3Apmid%2F33150344&rft.externalDBID=n%2Fa&rft.externalDocID=000591568400032 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1359-7345&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1359-7345&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1359-7345&client=summon |