Issue 23, 2014

A copper-catalyzed coupling reaction of vinyl halides and carbazates: application in the assembly of polysubstituted pyrroles

Abstract

CuI-catalyzed coupling of vinyl halides with carbazates gives N-protected N-alkenylhydrazines, which are condensed with ketones under acidic conditions to give polysubstituted pyrroles. The pyrrole synthesis may go through a similar mechanism with Fischer indole synthesis, which involves a [3,3]-sigmatropic rearrangement and other reactions.

Graphical abstract: A copper-catalyzed coupling reaction of vinyl halides and carbazates: application in the assembly of polysubstituted pyrroles

Supplementary files

Article information

Article type
Communication
Submitted
23 Dec 2013
Accepted
27 Jan 2014
First published
31 Jan 2014

Chem. Commun., 2014,50, 3085-3088

A copper-catalyzed coupling reaction of vinyl halides and carbazates: application in the assembly of polysubstituted pyrroles

C. Zhou and D. Ma, Chem. Commun., 2014, 50, 3085 DOI: 10.1039/C3CC49724K

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