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Chem Commun (Camb). 2014 Mar 21;50(23):3085-8. doi: 10.1039/c3cc49724k.

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

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1
School of Pharmacy, East China University of Science and Technology, 130 Meilong Lu, Shanghai 200037, China.

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.

PMID:
24514455
DOI:
10.1039/c3cc49724k
[Indexed for MEDLINE]
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