SYNTHESIS OF 1,3- AND 1,2,3-FUNCTIONALIZED PYRROLES <i>via</i> Ir(I)-CATALYZED VINYLATION OF ALLYL ALCOHOLS

Abstract

An efficient method for the preparation of 1,3-disubstituted and 1,2,3-trisubstituted pyrroles was developed through a sequence involving O-vinylation of allyl alcohols followed by Claisen rearrangement and further ozonolysis, concurring in a Paal–Knorr reaction with primary amines. Hg(II) and Ir(I) catalysts and different vinylating reagents were tested. The best results were consistently obtained with the [Ir(cod)Cl]₂–vinyl acetate system. The featured methodology gives access to functionalized pyrroles in overall good yields, whose chemical architecture may awake interest for assorted applications.