Gold-Catalyzed Formal Dehydro-Diels-Alder Reactions of Ene-Ynamide Derivatives Bearing Terminal Alkyne Chains

Qing Zhao; David Fabian León rayo; Dominic Campeau; Martin Daenen; Fabien Gagosz

doi:10.1002/anie.201807136

Journal articles

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

Domain :

Chemical Sciences / Organic chemistry

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https://hal-polytechnique.archives-ouvertes.fr/hal-02090677
Contributor : Aurélien Arnoux <>
Submitted on : Friday, April 5, 2019 - 9:24:30 AM
Last modification on : Tuesday, November 3, 2020 - 9:50:05 AM

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

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

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