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
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.
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Submitted on : Thursday, February 27, 2014 - 10:24:29 AM
Last modification on : Wednesday, December 11, 2019 - 8:16:01 AM

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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, Wiley-VCH Verlag, 2011, 50 (22), pp.5090-5094. ⟨10.1002/anie.201100327⟩. ⟨hal-00951233⟩

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