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Issue 7, 2012

A catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides: iodobenzene as an organocatalyst and m-chloroperbenzoic acid as a terminal oxidant

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Abstract

The first catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides, which probably involves in situ generation of a tetracoordinated bis(aqua)(hydroxy)phenyl-λ3-iodane complex as an active oxidant from a catalytic amount of iodobenzene by the reaction with m-chloroperbenzoic acid in the presence of HBF4 in dichloromethanewater under mild conditions, was developed.

Graphical abstract: A catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides: iodobenzene as an organocatalyst and m-chloroperbenzoic acid as a terminal oxidant

Supplementary files

Article information


Submitted
13 Oct 2011
Accepted
23 Nov 2011
First published
25 Nov 2011

Chem. Commun., 2012,48, 982-984
Article type
Communication

A catalytic version of hypervalent aryl-λ3-iodane-induced Hofmann rearrangement of primary carboxamides: iodobenzene as an organocatalyst and m-chloroperbenzoic acid as a terminal oxidant

K. Miyamoto, Y. Sakai, S. Goda and M. Ochiai, Chem. Commun., 2012, 48, 982 DOI: 10.1039/C2CC16360H

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