Catalyst-dependent divergent synthesis of pyrroles from 3-alkynyl imine derivatives: a noncarbonylative and carbonylative approach

Angew Chem Int Ed Engl. 2014 Aug 4;53(32):8492-7. doi: 10.1002/anie.201405215. Epub 2014 Jun 25.

Abstract

A novel Ru(0)- and Rh(I)-catalyzed noncarbonylative and carbonylative cycloisomerization of readily available 3-alkynyl imine derivatives has been developed to provide 3,4-fused or nonfused pyrrole derivatives efficiently in moderate to excellent yields. The key steps involve the formation of a ruthenium carbenoid intermediate or a rhodacycle intermediate, respectively. In these reactions, CO can serve as a ligand or a reagent.

Keywords: CC bond activation; pyrrole synthesis; rhodium; ring expansion; ruthenium.