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

S. Kramer (1) , Yann Odabachian (2) , J. Overgaard (1) , M. Rottländer (3) , Fabien Gagosz (2) , T. Skrydstrup (1)

1 Department of Chemistry [Aarhus]
2 DCSO - Laboratoire de synthèse organique
3 Division of Medicinal Chemistry

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.

Domains: Chemical Sciences; Organic chemistry

S. Kramer, Yann Odabachian, J. Overgaard, M. Rottländer, Fabien Gagosz, et al.. Taking advantage of the ambivalent reactivity of ynamides in gold catalysis: A rare case of alkyne dimerization. Angewandte Chemie International Edition, 2011, 50 (22), pp.5090-5094. ⟨10.1002/anie.201100327⟩. ⟨hal-00951233⟩