Abstract

During the last decade, gold-catalyzed reactions have become a tour de force in organic synthesis. Recently, the gold-, Brønsted acid- or Lewis acid-catalyzed oxygen transfer from carbonyl to carbon–carbon triple bond, the so-called alkyne–carbonyl metathesis, has attracted much attention because this atom economical transformation generates α,β-unsaturated carbonyl derivatives which are of great interest in synthetic organic chemistry. This mini-review focuses on the most recent achievements on gold-catalyzed oxygen transfer reactions of tethered alkynones, diynes or alkynyl epoxides to cyclic enones. The corresponding mechanisms for the transformations are also discussed.

Highlights

  • During the early years of this century, organic chemists became aware that gold salts or complexes were highly active catalysts in homogeneous catalysis because of the strong π- and σ-electrophilicity of gold [28-33]

  • The number of new gold-catalyzed reactions reported in the literature has increased substantially and gold catalysis has become one of the hottest research fields in synthetic organic chemistry [34-42]

  • Due to their unique alkynophilicity, gold catalysts are especially suited to the activation of carbon–carbon triple bonds

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Summary

Open Access

Address: Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, KY 40292, USA This article is part of the Thematic Series "Gold catalysis in organic synthesis". Keywords: alkyne–carbonyl metathesis; cyclic enones; gold-catalyzed; oxonium; oxygen transfer

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