Iodonium Salts Are Key Intermediates in Pd-Catalyzed Acetoxylation of Pyrroles

Lubriks, D.; Sokolovs, I.; Suna, E. Org. Lett. 2011, 13, 4324–4327.

DOI: 10.1021/ol201665c

Abstract

A mild, room-temperature Pd-catalyzed acetoxylation of pyrroles with phenyliodonium acetate is described. The acetoxylation was found to proceed via the initial formation of pyrrolyl(phenyl)iodonium acetates, which were converted to acetoxypyrroles in the presence of Pd(OAc)2. The acetoxylation could also be carried out as a one-pot sequential procedure without the isolation of the intermediate iodonium salts.