Issue 6, 2015

Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp3)–H bonds of acetonitriles involving 1,2-aryl migration

Abstract

A novel metal-free oxidative 1,2-alkylarylation of unactivated alkenes with the α-C(sp3)–H bonds of acetonitriles for the synthesis of 5-oxo-pentanenitriles is presented. In the presence of TBPB (tert-butyl peroxybenzoate), a variety of α-aryl allylic alcohols underwent the 1,2-alkylarylation reaction with acetonitriles, giving 5-oxo-pentanenitriles in good to excellent yields. This method proceeds via the C(sp3)–H oxidative coupling with the C–C double bond and 1,2-aryl-migration, and represents a new access to acyclic molecules through metal-free oxidative alkene 1,2-alkylarylation.

Graphical abstract: Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp3)–H bonds of acetonitriles involving 1,2-aryl migration

Supplementary files

Article information

Article type
Communication
Submitted
07 Nov 2014
Accepted
20 Nov 2014
First published
21 Nov 2014

Chem. Commun., 2015,51, 1024-1026

Oxidative radical 1,2-alkylarylation of alkenes with α-C(sp3)–H bonds of acetonitriles involving 1,2-aryl migration

Y. Li, B. Liu, H. Li, Q. Wang and J. Li, Chem. Commun., 2015, 51, 1024 DOI: 10.1039/C4CC08902B

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