Visible-Light-Induced Copper-Catalyzed Decarboxylative Coupling of Redox-Active Esters with N‑Heteroarenes
Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between N-heteroarenes and redox-active esters. Various N-hydroxyphthalimide esters reacted with isoquinoline, quinoline, pyridine, pyrimidine, quinazoline, phthalazine, phenanthridine, and pyr...
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| Published in | Organic letters Vol. 21; no. 14; pp. 5728 - 5732 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
19.07.2019
Amer Chemical Soc |
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| Online Access | Get full text |
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| Abstract | Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between N-heteroarenes and redox-active esters. Various N-hydroxyphthalimide esters reacted with isoquinoline, quinoline, pyridine, pyrimidine, quinazoline, phthalazine, phenanthridine, and pyridazine to give the corresponding products in modest to excellent yields. The reactions proceed under mild conditions and have a broad scope and high functional group tolerance. Mechanistic studies revealed that the catalytic behavior of CuI photocatalyst generated in situ was consistent with that of preformed [Cu(dmp)(xantphos)]BF4. |
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| AbstractList | Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between N-heteroarenes and redox-active esters. Various N-hydroxyphthalimide esters reacted with isoquinoline, quinoline, pyridine, pyrimidine, quinazoline, phthalazine, phenanthridine, and pyridazine to give the corresponding products in modest to excellent yields. The reactions proceed under mild conditions and have a broad scope and high functional group tolerance. Mechanistic studies revealed that the catalytic behavior of CuI photocatalyst generated in situ was consistent with that of preformed [Cu(dmp)(xantphos)]BF4. Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between N-heteroarenes and redox-active esters. Various N-hydroxyphthalimide esters reacted with isoquinoline, quinoline, pyridine, pyrimidine, quinazoline, phthalazine, phenanthridine, and pyridazine to give the corresponding products in modest to excellent yields. The reactions proceed under mild conditions and have a broad scope and high functional group tolerance. Mechanistic studies revealed that the catalytic behavior of CuI photocatalyst generated in situ was consistent with that of preformed [Cu(dmp)(xantphos)]BF4. Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between -heteroarenes and redox-active esters. Various -hydroxyphthalimide esters reacted with isoquinoline, quinoline, pyridine, pyrimidine, quinazoline, phthalazine, phenanthridine, and pyridazine to give the corresponding products in modest to excellent yields. The reactions proceed under mild conditions and have a broad scope and high functional group tolerance. Mechanistic studies revealed that the catalytic behavior of Cu photocatalyst generated in situ was consistent with that of preformed [Cu(dmp)(xantphos)]BF . Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between N-heteroarenes and redox-active esters. Various N-hydroxyphthalimide esters reacted with isoquinoline, quinoline, pyridine, pyrimidine, quinazoline, phthalazine, phenanthridine, and pyridazine to give the corresponding products in modest to excellent yields. The reactions proceed under mild conditions and have a broad scope and high functional group tolerance. Mechanistic studies revealed that the catalytic behavior of Cu-I photocatalyst generated in situ was consistent with that of preformed [Cu(dmp)(xantphos)]BF4. |
| Author | Huang, Shi-Sheng Song, Hong-Jian Lyu, Xue-Li Liu, Yu-Xiu Wang, Qing-Min |
| AuthorAffiliation | State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) |
| AuthorAffiliation_xml | – name: Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) – name: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry |
| Author_xml | – sequence: 1 givenname: Xue-Li surname: Lyu fullname: Lyu, Xue-Li organization: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry – sequence: 2 givenname: Shi-Sheng surname: Huang fullname: Huang, Shi-Sheng organization: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry – sequence: 3 givenname: Hong-Jian surname: Song fullname: Song, Hong-Jian organization: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry – sequence: 4 givenname: Yu-Xiu surname: Liu fullname: Liu, Yu-Xiu organization: State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry – sequence: 5 givenname: Qing-Min orcidid: 0000-0002-6062-3766 surname: Wang fullname: Wang, Qing-Min email: wangqm@nankai.edu.cn organization: Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31251074$$D View this record in MEDLINE/PubMed |
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| Keywords | IRIDIUM COMPLEXES ALKYLATION PHOTOCATALYSIS PHOTOPOLYMERIZATION ALDEHYDES N-(ACYLOXY)PHTHALIMIDE TRANSFORMATIONS CYCLIZATION PHOTOREDOX CATALYSIS CARBOXYLIC-ACIDS |
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| Snippet | Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between N-heteroarenes and redox-active esters.... Herein we report a protocol for visible-light-induced copper-catalyzed decarboxylative coupling reactions between -heteroarenes and redox-active esters.... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Visible-Light-Induced Copper-Catalyzed Decarboxylative Coupling of Redox-Active Esters with N‑Heteroarenes |
| URI | http://dx.doi.org/10.1021/acs.orglett.9b02105 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000476957200074 https://www.ncbi.nlm.nih.gov/pubmed/31251074 https://search.proquest.com/docview/2250638974 |
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