Gold-Catalyzed Formal Dehydro-Diels-Alder Reactions of Ene-Ynamide Derivatives Bearing Terminal Alkyne Chains: Scope and Mechanistic Studies

Qing Zhao 1 David Fabian León rayo 2 Dominic Campeau 2 Martin Daenen 2 Fabien Gagosz 1, 2
1 DCSO - Laboratoire de synthèse organique
2 Department of Chemistry and Biomolecular Sciences University of Ottawa, D'lorio Hall
Abstract : A new protocol for the synthesis of a variety of N-containing aromatic heterocycles by a formal gold-catalyzed dehydro-Diels-Alder reaction of ynamide derivatives has been developed. Deuterium-labeling experiments and kinetic studies support the involvement of a dual gold catalysis mechanism in which a gold acetylide moiety adds onto an aurated keteneiminium.
Keywords : cycloaddition gold heterocycles reaction kinetics reaction mechanisms
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Journal articles
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Submitted on : Friday, April 5, 2019 - 9:24:30 AM
Last modification on : Friday, April 12, 2019 - 1:31:50 AM

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Qing Zhao, David Fabian León rayo, Dominic Campeau, Martin Daenen, Fabien Gagosz. Gold-Catalyzed Formal Dehydro-Diels-Alder Reactions of Ene-Ynamide Derivatives Bearing Terminal Alkyne Chains: Scope and Mechanistic Studies. Angewandte Chemie International Edition, Wiley-VCH Verlag, 2018, 57 (41), pp.13603-13607. ⟨10.1002/anie.201807136⟩. ⟨hal-02090677⟩

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