Synthesis of acyl pyrroles via palladium-catalyzed carbonylative amination of aryl and alkenyl iodides

Stephanie Ho; Ganna Bondarenko; David Rosa; Bojan Dragisic; Arturo Orellana

doi:10.1021/jo2022444

Synthesis of acyl pyrroles via palladium-catalyzed carbonylative amination of aryl and alkenyl iodides

J Org Chem. 2012 Feb 17;77(4):2008-12. doi: 10.1021/jo2022444. Epub 2012 Feb 7.

Authors

Stephanie Ho¹, Ganna Bondarenko, David Rosa, Bojan Dragisic, Arturo Orellana

Affiliation

¹ Department of Chemistry, York University, 440 Chemistry Building 4700 Keele Street, Toronto, ON, Canada M3J 1P3.

PMID: 22242808
DOI: 10.1021/jo2022444

Abstract

A palladium-catalyzed synthesis of acyl pyrroles from aryl and alkenyl iodides is reported. This carbonylative amination requires only atmospheric (balloon) pressure of carbon monoxide and proceeds with Pd(PPh(3))(4) and Pd-NHC catalysts. Aryl and heteroaryl iodides give the corresponding acyl pyrroles in good to excellent yields, while alkenyl iodides provide the corresponding acyl pyrroles in low to moderate yields.