Exploring new applications of the hypervalent iodine reagent PIFA [bis(trifluoroacetoxy)iodobenzene] in the construction of pyrrolidine heterocycles

Abstract

In this paper the benefits of the oxidative properties of PIFA –one of the most generally employed hypervalent iodine reagents oriented to the preparation of a number of pyrrolidine heterocycles from properly substituted amides will be disclosed. The intramolecular reaction of the resultant electrophilic N-acylnitrenium intermediate with an olefin or alkyne fragment will facilitate the formation of the required C–N connection. The absence of any metal source in the I(III)-mediated olefin- or alkyne- intramolecular amidation step, and the structural versatility of the final heterocycles that are prepared, feature the present methodology.