Iodonium salts are key intermediates in Pd-catalyzed acetoxylation of pyrroles

Dmitrijs Lubriks; Igors Sokolovs; Edgars Suna

doi:10.1021/ol201665c

Iodonium salts are key intermediates in Pd-catalyzed acetoxylation of pyrroles

Org Lett. 2011 Aug 19;13(16):4324-7. doi: 10.1021/ol201665c. Epub 2011 Jul 20.

Authors

Dmitrijs Lubriks¹, Igors Sokolovs, Edgars Suna

Affiliation

¹ Latvian Institute of Organic Synthesis, Aizkraukles 21, LV-1006, Riga, Latvia.

PMID: 21774523
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.