Energy Transfer to Ni-Amine Complexes in Dual Catalytic, Light-Driven C-N Cross-Coupling Reactions
Dual catalytic light-driven cross-coupling methodologies utilizing a Ni(II) salt with a photocatalyst (PC) have emerged as promising methodologies to forge aryl C-N bonds under mild conditions. The recent discovery that the PC can be omitted and the Ni(II) complex directly photoexcited suggests that...
Gespeichert in:
| Veröffentlicht in: | Journal of the American Chemical Society Jg. 141; H. 49; S. 19479 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Journal Article |
| Sprache: | Englisch |
| Veröffentlicht: |
United States
11.12.2019
|
| ISSN: | 1520-5126, 1520-5126 |
| Online-Zugang: | Weitere Angaben |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| Abstract | Dual catalytic light-driven cross-coupling methodologies utilizing a Ni(II) salt with a photocatalyst (PC) have emerged as promising methodologies to forge aryl C-N bonds under mild conditions. The recent discovery that the PC can be omitted and the Ni(II) complex directly photoexcited suggests that the PC may perform energy transfer (EnT) to the Ni(II) complex, a mechanistic possibility that has recently been proposed in other systems across dual Ni photocatalysis. Here, we report the first studies in this field capable of distinguishing EnT from electron transfer (ET), and the results are consistent with Förster-type EnT from the excited state [Ru(bpy)
]Cl
PC to Ni-amine complexes. The structure and speciation of Ni-amine complexes that are the proposed EnT acceptors were elucidated by crystallography and spectroscopic binding studies. With the acceptors known, quantitative Förster theory was utilized to predict the ratio of quenching rate constants upon changing the PC, enabling selection of an organic phenoxazine PC that proved to be more effective in catalyzing C-N cross-coupling reactions with a diverse selection of amines and aryl halides. |
|---|---|
| AbstractList | Dual catalytic light-driven cross-coupling methodologies utilizing a Ni(II) salt with a photocatalyst (PC) have emerged as promising methodologies to forge aryl C-N bonds under mild conditions. The recent discovery that the PC can be omitted and the Ni(II) complex directly photoexcited suggests that the PC may perform energy transfer (EnT) to the Ni(II) complex, a mechanistic possibility that has recently been proposed in other systems across dual Ni photocatalysis. Here, we report the first studies in this field capable of distinguishing EnT from electron transfer (ET), and the results are consistent with Förster-type EnT from the excited state [Ru(bpy)
]Cl
PC to Ni-amine complexes. The structure and speciation of Ni-amine complexes that are the proposed EnT acceptors were elucidated by crystallography and spectroscopic binding studies. With the acceptors known, quantitative Förster theory was utilized to predict the ratio of quenching rate constants upon changing the PC, enabling selection of an organic phenoxazine PC that proved to be more effective in catalyzing C-N cross-coupling reactions with a diverse selection of amines and aryl halides. Dual catalytic light-driven cross-coupling methodologies utilizing a Ni(II) salt with a photocatalyst (PC) have emerged as promising methodologies to forge aryl C-N bonds under mild conditions. The recent discovery that the PC can be omitted and the Ni(II) complex directly photoexcited suggests that the PC may perform energy transfer (EnT) to the Ni(II) complex, a mechanistic possibility that has recently been proposed in other systems across dual Ni photocatalysis. Here, we report the first studies in this field capable of distinguishing EnT from electron transfer (ET), and the results are consistent with Förster-type EnT from the excited state [Ru(bpy)3]Cl2 PC to Ni-amine complexes. The structure and speciation of Ni-amine complexes that are the proposed EnT acceptors were elucidated by crystallography and spectroscopic binding studies. With the acceptors known, quantitative Förster theory was utilized to predict the ratio of quenching rate constants upon changing the PC, enabling selection of an organic phenoxazine PC that proved to be more effective in catalyzing C-N cross-coupling reactions with a diverse selection of amines and aryl halides.Dual catalytic light-driven cross-coupling methodologies utilizing a Ni(II) salt with a photocatalyst (PC) have emerged as promising methodologies to forge aryl C-N bonds under mild conditions. The recent discovery that the PC can be omitted and the Ni(II) complex directly photoexcited suggests that the PC may perform energy transfer (EnT) to the Ni(II) complex, a mechanistic possibility that has recently been proposed in other systems across dual Ni photocatalysis. Here, we report the first studies in this field capable of distinguishing EnT from electron transfer (ET), and the results are consistent with Förster-type EnT from the excited state [Ru(bpy)3]Cl2 PC to Ni-amine complexes. The structure and speciation of Ni-amine complexes that are the proposed EnT acceptors were elucidated by crystallography and spectroscopic binding studies. With the acceptors known, quantitative Förster theory was utilized to predict the ratio of quenching rate constants upon changing the PC, enabling selection of an organic phenoxazine PC that proved to be more effective in catalyzing C-N cross-coupling reactions with a diverse selection of amines and aryl halides. |
| Author | Kudisch, Max Thordarson, Pall Miyake, Garret M Lim, Chern-Hooi |
| Author_xml | – sequence: 1 givenname: Max surname: Kudisch fullname: Kudisch, Max organization: Department of Chemistry , Colorado State University , Fort Collins , Colorado 80523 , United States – sequence: 2 givenname: Chern-Hooi orcidid: 0000-0003-1823-6305 surname: Lim fullname: Lim, Chern-Hooi organization: New Iridium LLC , Boulder , Colorado 80303 , United States – sequence: 3 givenname: Pall orcidid: 0000-0002-1200-8814 surname: Thordarson fullname: Thordarson, Pall organization: School of Chemistry, The Australian Centre for Nanomedicine and the ARC Centre of Excellence in Convergent Bio-Nano Science & Technology , The University of New South Wales , Sydney , NSW 2052 , Australia – sequence: 4 givenname: Garret M orcidid: 0000-0003-2451-7090 surname: Miyake fullname: Miyake, Garret M organization: Department of Chemistry , Colorado State University , Fort Collins , Colorado 80523 , United States |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31714761$$D View this record in MEDLINE/PubMed |
| BookMark | eNpNkM1LwzAchoNM3IfePEuOHsxs0iRtj6ObHzAmyDyXtP11ZrRJTdLh_nsHTvD0PoeH5_BO0chYAwjd0mhOI0Yf96ry86ykNOLZBZpQwSIiKJOjfzxGU-_3URRxltIrNI5pQnki6QSVKwNud8Rbp4xvwOFg8UaTRacN4Nx2fQvf4LE2eDmoFucqqPYYdPWA13r3GcjS6QMYnJMNzp31nuR26FttdvgdVBW0Nf4aXTaq9XBz3hn6eFpt8xeyfnt-zRdrooSIA4FSglQ1q2TNFJdNmioeV5yJ-kSJYIyWZS1TYKUAWYsMmiyuk4xL1VAGlWQzdP_b7Z39GsCHotO-grZVBuzgCxbTU41ncXZS787qUHZQF73TnXLH4u8X9gMbzmYT |
| CitedBy_id | crossref_primary_10_1002_anie_202012877 crossref_primary_10_1021_jacs_3c02784 crossref_primary_10_1039_D0SE01454K crossref_primary_10_1002_chem_202300458 crossref_primary_10_1002_adsc_202001176 crossref_primary_10_1002_anie_202310470 crossref_primary_10_1021_jacs_0c07600 crossref_primary_10_1002_chem_202203394 crossref_primary_10_1021_acsami_5c07227 crossref_primary_10_1038_s41467_025_60729_x crossref_primary_10_1002_ange_202219107 crossref_primary_10_1021_jacs_0c00286 crossref_primary_10_1039_D1SC05113J crossref_primary_10_1002_chem_202202385 crossref_primary_10_1021_jacs_0c05901 crossref_primary_10_1002_cctc_202200477 crossref_primary_10_1002_anie_202218908 crossref_primary_10_1002_anie_202103803 crossref_primary_10_1021_jacs_2c08838 crossref_primary_10_1039_D3SC02588H crossref_primary_10_1038_s41467_022_29781_9 crossref_primary_10_1039_D2SC02174A crossref_primary_10_1002_ange_202012877 crossref_primary_10_1002_chem_202003974 crossref_primary_10_1007_s10562_022_04255_1 crossref_primary_10_1002_chem_202002800 crossref_primary_10_1021_jacs_4c03099 crossref_primary_10_1021_jacs_1c04652 crossref_primary_10_1038_s41557_022_01008_w crossref_primary_10_1002_anie_202200352 crossref_primary_10_1021_jacs_3c10792 crossref_primary_10_1021_jacs_2c01814 crossref_primary_10_1021_jacs_9b12835 crossref_primary_10_1002_ejoc_202300933 crossref_primary_10_1021_acscatal_5c03251 crossref_primary_10_1021_jacs_2c03835 crossref_primary_10_1021_acscatal_4c07185 crossref_primary_10_1039_D3SC02440G crossref_primary_10_1002_anie_202108587 crossref_primary_10_1038_s41467_025_58687_5 crossref_primary_10_1002_cjoc_202401238 crossref_primary_10_1021_acs_inorgchem_5c01586 crossref_primary_10_1038_s41929_024_01160_1 crossref_primary_10_1002_ange_202013852 crossref_primary_10_1002_chem_202000052 crossref_primary_10_1002_ange_202200352 crossref_primary_10_1016_j_trechm_2023_05_001 crossref_primary_10_1016_j_chempr_2022_10_010 crossref_primary_10_1021_jacs_2c06993 crossref_primary_10_1021_jacs_2c13409 crossref_primary_10_1021_jacs_0c02848 crossref_primary_10_1039_D2QI00173J crossref_primary_10_1039_D4QO01686F crossref_primary_10_1039_D5QO00660K crossref_primary_10_1002_chem_202004492 crossref_primary_10_1039_D4SC04196H crossref_primary_10_1002_cssc_202201094 crossref_primary_10_1038_s41929_020_0473_6 crossref_primary_10_1021_jacs_0c06139 crossref_primary_10_1002_ange_202108587 crossref_primary_10_1021_jacs_0c00781 crossref_primary_10_1016_j_jcat_2025_115972 crossref_primary_10_1002_cjoc_202300500 crossref_primary_10_1021_jacs_2c06831 crossref_primary_10_1016_j_tet_2020_131861 crossref_primary_10_1021_jacs_2c09745 crossref_primary_10_1039_D0RE00036A crossref_primary_10_1073_pnas_2119267119 crossref_primary_10_1021_jacs_1c12059 crossref_primary_10_1039_D2QO01134D crossref_primary_10_1055_a_1946_0512 crossref_primary_10_1039_D0RA08749A crossref_primary_10_1039_D2QO01700H crossref_primary_10_1002_ange_202310470 crossref_primary_10_1002_anie_202013852 crossref_primary_10_1016_j_cogsc_2020_05_001 crossref_primary_10_1038_s41929_020_00553_2 crossref_primary_10_1016_j_trechm_2025_08_003 crossref_primary_10_1016_j_chempr_2022_05_011 crossref_primary_10_1007_s11426_023_1911_x crossref_primary_10_1002_cctc_202200485 crossref_primary_10_1002_cctc_202500964 crossref_primary_10_1002_adsc_202100030 crossref_primary_10_1002_ange_202218908 crossref_primary_10_1002_anie_202219107 crossref_primary_10_1007_s43630_022_00181_8 crossref_primary_10_1021_acscatal_4c07962 crossref_primary_10_1021_jacs_0c10882 crossref_primary_10_1002_ange_202103803 |
| ContentType | Journal Article |
| DBID | NPM 7X8 |
| DOI | 10.1021/jacs.9b11049 |
| DatabaseName | PubMed MEDLINE - Academic |
| DatabaseTitle | PubMed MEDLINE - Academic |
| DatabaseTitleList | PubMed 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: 7X8 name: MEDLINE - Academic url: https://search.proquest.com/medline sourceTypes: Aggregation Database |
| DeliveryMethod | no_fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1520-5126 |
| ExternalDocumentID | 31714761 |
| Genre | Journal Article |
| GrantInformation_xml | – fundername: NIGMS NIH HHS grantid: R35 GM119702 |
| GroupedDBID | --- -DZ -ET -~X .DC .K2 4.4 53G 55A 5GY 5RE 5VS 7~N 85S AABXI AAHBH ABJNI ABMVS ABPPZ ABQRX ABUCX ACBEA ACGFO ACGFS ACJ ACNCT ACS ADHLV AEESW AENEX AFEFF AGXLV AHGAQ ALMA_UNASSIGNED_HOLDINGS AQSVZ BAANH BKOMP CS3 CUPRZ DU5 EBS ED~ F5P GGK GNL IH2 IH9 JG~ LG6 NPM P2P ROL RXW TAE TN5 UHB UI2 UKR UPT VF5 VG9 VQA W1F WH7 XSW YIN YQT YZZ ZCA ~02 7X8 AAYWT ABBLG ABLBI ABUFD AETEA AHDLI |
| ID | FETCH-LOGICAL-a553t-eb6e6ad2c6d2a46f88a43c425d88a75221bbd68e2b5e6d59ef93d7946af12ec62 |
| IEDL.DBID | 7X8 |
| ISICitedReferencesCount | 137 |
| ISICitedReferencesURI | http://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestLinkType=CitingArticles&DestApp=WOS_CPL&KeyUT=000502687800037&url=https%3A%2F%2Fcvtisr.summon.serialssolutions.com%2F%23%21%2Fsearch%3Fho%3Df%26include.ft.matches%3Dt%26l%3Dnull%26q%3D |
| ISSN | 1520-5126 |
| IngestDate | Sun Nov 09 11:39:13 EST 2025 Wed Feb 19 02:30:53 EST 2025 |
| IsDoiOpenAccess | false |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 49 |
| Language | English |
| LinkModel | DirectLink |
| MergedId | FETCHMERGED-LOGICAL-a553t-eb6e6ad2c6d2a46f88a43c425d88a75221bbd68e2b5e6d59ef93d7946af12ec62 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0003-2451-7090 0000-0002-1200-8814 0000-0003-1823-6305 |
| OpenAccessLink | https://www.ncbi.nlm.nih.gov/pmc/articles/6941585 |
| PMID | 31714761 |
| PQID | 2314254939 |
| PQPubID | 23479 |
| ParticipantIDs | proquest_miscellaneous_2314254939 pubmed_primary_31714761 |
| PublicationCentury | 2000 |
| PublicationDate | 2019-12-11 |
| PublicationDateYYYYMMDD | 2019-12-11 |
| PublicationDate_xml | – month: 12 year: 2019 text: 2019-12-11 day: 11 |
| PublicationDecade | 2010 |
| PublicationPlace | United States |
| PublicationPlace_xml | – name: United States |
| PublicationTitle | Journal of the American Chemical Society |
| PublicationTitleAlternate | J Am Chem Soc |
| PublicationYear | 2019 |
| SSID | ssj0004281 |
| Score | 2.6297314 |
| Snippet | Dual catalytic light-driven cross-coupling methodologies utilizing a Ni(II) salt with a photocatalyst (PC) have emerged as promising methodologies to forge... |
| SourceID | proquest pubmed |
| SourceType | Aggregation Database Index Database |
| StartPage | 19479 |
| Title | Energy Transfer to Ni-Amine Complexes in Dual Catalytic, Light-Driven C-N Cross-Coupling Reactions |
| URI | https://www.ncbi.nlm.nih.gov/pubmed/31714761 https://www.proquest.com/docview/2314254939 |
| Volume | 141 |
| WOSCitedRecordID | wos000502687800037&url=https%3A%2F%2Fcvtisr.summon.serialssolutions.com%2F%23%21%2Fsearch%3Fho%3Df%26include.ft.matches%3Dt%26l%3Dnull%26q%3D |
| hasFullText | |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| link | http://cvtisr.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwpV1bS8MwFA7qBH3xfpk3IvhonG3atH2S0W34MMsQhb2NpDmRibZz3UT_vSdthz6J4EvpS0OTnn7fl8v5DiEXxhWulqFmkGrNvNAXTKFSZtJBLko1D6Ayce0HSRIOh9GgXnAr6mOVC0wsgVrnqV0jb6EO8exkhkc3kzdmq0bZ3dW6hMYyaXCUMjaqg-EPt3A3rPxScYqExCbqg-9Ia61nmRZXkULy834RlyXJ9Db_-3pbZKOWl7RdxcM2WYJsh6zFi6puu0R1y2Q_WnKUgSmd5TQZs_Yrqk1qweEFPqCg44x25thQbFd3PrGxS9ovLUc6UwuPNGYJjS3Bsjif26TeJ3oPVY5EsUcee92H-JbVdRaY9H0-Y6AECKndVGhXesKEofR4it3ReBegQHOU0iIEV_kgtB-Bibi2xvTSOC6kwt0nK1mewSGhiiN-aDDG5r9GgaOuOUKI5kr7xgulaJLzxfCNsON2c0JmkM-L0fcANslB9Q1Gk8pwY8RtlfZAOEd_ePqYrKOmKUs8OM4JaRj8i-GUrKbvs3ExPSsDBK_J4O4LQ5_F3A |
| 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=Energy+Transfer+to+Ni-Amine+Complexes+in+Dual+Catalytic%2C+Light-Driven+C-N+Cross-Coupling+Reactions&rft.jtitle=Journal+of+the+American+Chemical+Society&rft.au=Kudisch%2C+Max&rft.au=Lim%2C+Chern-Hooi&rft.au=Thordarson%2C+Pall&rft.au=Miyake%2C+Garret+M&rft.date=2019-12-11&rft.issn=1520-5126&rft.eissn=1520-5126&rft.volume=141&rft.issue=49&rft.spage=19479&rft_id=info:doi/10.1021%2Fjacs.9b11049&rft.externalDBID=NO_FULL_TEXT |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=1520-5126&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=1520-5126&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=1520-5126&client=summon |