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Taking Advantage of the Ambivalent Reactivity of Ynamides in Gold Catalysis: A Rare Case of Alkyne Dimerization


  • We are deeply appreciative of generous financial support from the Carlsberg Foundation, the Danish National Research Foundation, H. Lundbeck A/S, the OChem Graduate School, the Ecole Polytechnique and Aarhus University.


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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).