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A copper-catalyzed coupling reaction of vinyl halides and carbazates: application in the assembly of polysubstituted pyrroles†
Chemical Communications Pub Date : 01/31/2014 00:00:00 , DOI:10.1039/C3CC49724K
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
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