Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 36, Pages 11792-11796Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201807303
Keywords
alkenes; C-H functionalization; cyanation; hypervalent compounds; synthetic methods
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Funding
- European Research Council (ERC) [692640]
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A metal-free and direct alkene C-H cyanation is described. Directing groups are not required and the mechanism involves electrophilic activation of the alkene by a cyano iodine(III) species generated in situ from a [bis(trifluoroacetoxy)iodo]arene and trimethylsilyl cyanide as the cyanide source. This C-H functionalization can be conducted on gram scale, and for noncyclic 1,1- and 1,2-disubstuted alkenes high stereoselectivity is achieved, thus rendering the method highly valuable.
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