4.8 Article

Gold-Catalyzed Cascade Cyclization-Oxidative Alkynylation of Allenoates

Journal

ORGANIC LETTERS
Volume 12, Issue 21, Pages 4904-4907

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol102061k

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Funding

  1. GlaxoSmithKline
  2. EPSRC

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A gold(I)-catalyzed cascade-cyclization oxidative cross-coupling process has been applied to prepare beta-alkynyl-y-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.

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