Taking advantage of the ambivalent reactivity of ynamides in gold catalysis: A rare case of alkyne dimerization

Abstract : A gold mine of results: A series of ynamides have been dimerized in the presence of a gold(I) complex. This unprecedented transformation involves the formation of a key keteniminium intermediate that reacts to form a variety of cyclic and acyclic products. The substitution pattern of the ynamide determines which product is formed (see scheme; EWG=electron-withdrawing group, Ts=p-toluenesulfonyl). Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.