Synfacts 2007(6): 0642-0642  
DOI: 10.1055/s-2007-968535
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Substituted Pyrroles via Cu-Catalyzed Vinylation of Hydrazides

Contributor(s): Paul Knochel, Andrei Gavryushin
M. Rodríguez Rivero, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
Further Information

Publication History

Publication Date:
22 May 2007 (online)

Significance

Pyrroles are found in many naturally occurring molecules. They are also widely used in modern material science. The authors developed a new convenient synthesis of polysubstituted pyrroles, consisting of a novel Cu-catalyzed bis-vinylation of Boc-hydrazines followed by the Piloty-Robinson rearrangement-cyclization of ketazines. It allows a flexible and regioselective preparation of a variety of functionalized pyrroles from simple and readily available precursors.