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Chem Commun (Camb). 2015 Jun 21;51(49):9969-71. doi: 10.1039/c5cc02968f.

A radical anti-Markovnikov addition of alkyl nitriles to simple alkenes via selective sp(3) C-H bond functionalization.

Chemical communications (Cambridge, England)

Zejiang Li, Yingxia Xiao, Zhong-Quan Liu

Affiliations

  1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, Gansu 730000, P. R. China. [email protected].

PMID: 25997410 DOI: 10.1039/c5cc02968f

Abstract

An efficient hydrocyanoalkylation of unactivated alkenes with alkyl nitriles was developed. Through this free-radical-initiated selective activation of the α-C(sp(3))-H bond of acetonitriles, an anti-Markovnikov addition of an α-cyano C-centered radical to olefins has been achieved, which allows a facile and convenient access to functionalized nitriles in large scales.

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