Issue 11, 2014

Water promoted C–C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC)

Abstract

A simple and highly efficient synthetic strategy to access 3,3-bipyrrole derivatives by the reaction of dienone derivatives with TosMIC is reported. The reaction involves a van Leusen's pyrrole synthesis followed by an unusual C–C bond cleavage in the presence of water under mild conditions.

Graphical abstract: Water promoted C–C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC)

Supplementary files

Article information

Article type
Paper
Submitted
02 Dec 2013
Accepted
15 Jan 2014
First published
15 Jan 2014

Org. Biomol. Chem., 2014,12, 1735-1740

Water promoted C–C bond cleavage: facile synthesis of 3,3-bipyrrole derivatives from dienones and tosylmethyl isocyanide (TosMIC)

R. Wang, S. Wang and S. Ji, Org. Biomol. Chem., 2014, 12, 1735 DOI: 10.1039/C3OB42570C

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