Catalytic Diverse Radical-Mediated 1,2-Cyanofunctionalization of Unactivated Alkenes via Synergistic Remote Cyano Migration and Protected Strategies
A catalytic radical protocol for 1,2-cyanofunctionalization of unactivated alkenes involving remote cyano migration triggered by addition of diverse carbon- and heteroatom-centered radicals to alkenes has been developed. This powerful strategy provides a diverse platform for the collection of a vari...
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| Published in | Organic letters Vol. 18; no. 23; pp. 6026 - 6029 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
02.12.2016
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | A catalytic radical protocol for 1,2-cyanofunctionalization of unactivated alkenes involving remote cyano migration triggered by addition of diverse carbon- and heteroatom-centered radicals to alkenes has been developed. This powerful strategy provides a diverse platform for the collection of a variety of synthetically important β-functionalized alkyl nitriles bearing densely functionalized carbonyl, cyano, and other various functional groups within the same molecules. The substrates TMS (trimethylsilyl)-protected alkenyl cyanohydrins are straightforwardly accessible via simple cyanosilylation of the corresponding ketones. |
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| AbstractList | A catalytic radical protocol for 1,2-cyanofunctionalization of unactivated alkenes involving remote cyano migration triggered by addition of diverse carbon- and heteroatom-centered radicals to alkenes has been developed. This powerful strategy provides a diverse platform for the collection of a variety of synthetically important β-functionalized alkyl nitriles bearing densely functionalized carbonyl, cyano, and other various functional groups within the same molecules. The substrates TMS (trimethylsilyl)-protected alkenyl cyanohydrins are straightforwardly accessible via simple cyanosilylation of the corresponding ketones. A catalytic radical protocol for 1,2-cyanofunctionalization of unactivated alkenes involving remote cyano migration triggered by addition of diverse carbon- and heteroatom-centered radicals to alkenes has been developed. This powerful strategy provides a diverse platform for the collection of a variety of synthetically important beta-functionalized alkyl nitriles bearing densely functionalized carbonyl, cyano, and other various functional groups within the same molecules. The substrates TMS (trimethylsilyl)-protected alkenyl cyanohydrins are straightforwardly accessible via simple cyanosilylation of the corresponding ketones. |
| Author | Liu, Xin-Yuan Li, Zhong-Liang Yang, Ning-Yuan Zhang, Hong-Xia Guo, Zhen Wang, Na Li, Lei |
| AuthorAffiliation | Department of Chemistry South University of Science and Technology of China College of Materials Science & Engineering, Key Laboratory of Interface Science and Engineering in Advanced Materials, Ministry of Education |
| AuthorAffiliation_xml | – name: South University of Science and Technology of China – name: College of Materials Science & Engineering, Key Laboratory of Interface Science and Engineering in Advanced Materials, Ministry of Education – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Na surname: Wang fullname: Wang, Na – sequence: 2 givenname: Lei surname: Li fullname: Li, Lei – sequence: 3 givenname: Zhong-Liang surname: Li fullname: Li, Zhong-Liang – sequence: 4 givenname: Ning-Yuan surname: Yang fullname: Yang, Ning-Yuan – sequence: 5 givenname: Zhen surname: Guo fullname: Guo, Zhen email: guozhen@tyut.edu.cn – sequence: 6 givenname: Hong-Xia surname: Zhang fullname: Zhang, Hong-Xia – sequence: 7 givenname: Xin-Yuan orcidid: 0000-0002-6978-6465 surname: Liu fullname: Liu, Xin-Yuan email: liuxy3@sustc.edu.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/27934336$$D View this record in MEDLINE/PubMed |
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| Keywords | VISIBLE-LIGHT ORGANIC-SYNTHESIS ALPHA-PERACETOXYNITRILES REDUCTIVE DECYANATION LIGHT PHOTOREDOX CATALYSIS ATOM-TRANSFER CARBONYL-COMPOUNDS C-H FUNCTIONALIZATION TRIFLUOROMETHYLTHIOLATION REACTIONS FLUOROALKYLSULFONYL CHLORIDES |
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| Snippet | A catalytic radical protocol for 1,2-cyanofunctionalization of unactivated alkenes involving remote cyano migration triggered by addition of diverse carbon-... |
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| SubjectTerms | alkenes chemical reactions Chemistry Chemistry, Organic free radicals ketones moieties nitriles Physical Sciences Science & Technology |
| Title | Catalytic Diverse Radical-Mediated 1,2-Cyanofunctionalization of Unactivated Alkenes via Synergistic Remote Cyano Migration and Protected Strategies |
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