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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Bibliographic Details
Published inOrganic letters Vol. 18; no. 23; pp. 6026 - 6029
Main Authors Wang, Na, Li, Lei, Li, Zhong-Liang, Yang, Ning-Yuan, Guo, Zhen, Zhang, Hong-Xia, Liu, Xin-Yuan
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.12.2016
Amer Chemical Soc
Subjects
alkenes
chemical reactions
Chemistry
Chemistry, Organic
free radicals
ketones
moieties
nitriles
Physical Sciences
Science & Technology
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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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.6b02960