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Org Lett. 2005 Jul 21;7(15):3279-81.

Indium triflate-catalyzed vinylation of beta-ketoesters with acetylene gas.

Author information

1
Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Japan.

Abstract

[reaction: see text]. An In(OTf)(3)-catalyzed addition of a beta-ketoester to acetylene in the presence of molecular sieves produces a alpha-vinylated ketoester in good to excellent yield. The vinylation reaction proceeds without any loss of elements in starting molecules under solvent-free conditions and allows the use of welding-grade acetylene, providing a practical method for synthetic utilization of acetylene gas.

PMID:
16018640
DOI:
10.1021/ol051057z

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