Synfacts 2007(5): 0474-0474  
DOI: 10.1055/s-2007-968470
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Rh-Catalyzed Synthesis of N-Aryl Trisubstituted Pyrroles

Contributor(s): Victor Snieckus, Kristoffer Månsson
C. V. Galliford, K. A. Scheidt*
Northwestern University, Evanston, USA
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Publication History

Publication Date:
24 April 2007 (online)


A new Rh-catalyzed route to 1,2-diaryl-substituted pyrroles in a three-component assembly reaction is reported. The combination of rhodium(II) salt with excess of diazoacetonitrile leads to the formation of a metallocarbenoid species which, in the presence of an imine, leads to the generation of an azomethine ylide. The reactive ylide intermediate is trapped by an activated acetylene diester in a [3+2] cycloaddition to form the 1,2-diaryl pyrroles in moderate to good yields. Notable is that only 1 mol% catalyst is needed for this transformation.