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Metal-Free Direct C-H Cyanation of Alkenes.

ABSTRACT: 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.

SUBMITTER: Wang X

PROVIDER: S-EPMC6175092 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Metal-Free Direct C-H Cyanation of Alkenes.

Wang Xi X Studer Armido A

Angewandte Chemie (International ed. in English) 20180806 36

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. ...[more]

PMID: 29995341

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