Gold-catalyzed cascade cyclization-oxidative alkynylation of allenoates.

Hopkinson MN, Ross JE, Giuffredi GT, Gee AD, Gouverneur V

A gold(I)-catalyzed cascade cyclization-oxidative cross-coupling process has been applied to prepare β-alkynyl-γ-butenolides directly from allenoates and various terminal alkynes. Following an initial gold-catalyzed C-O bond forming allenoate cyclization, a mechanism based on a Au(I)/Au(III) redox cycle has been proposed with Selectfluor acting as the external oxidant.

Keywords:

Alkynes

,

Catalysis

,

Crystallography, X-Ray

,

Cyclization

,

Gold

,

Models, Molecular

,

Molecular Structure

,

Naphthalenes

,

Oxidation-Reduction