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Practical Method for Transforming Alkynes into α-Diketones

Zhonghui Wan,* Chauncey D. Jones, David Mitchell, John Y. Pu and Tony Y. Zhang

*Global Chemical Process Research and Development, Eli Lilly and Company, Lilly Corporate Center, Indianapolis, Indiana 46285, wanzhlilly.com

Z. Wan, C. D. Jones, D. Mitchell, J. Y. Pu, T. Y. Zhang, J. Org. Chem., 2006, 71, 826-828.

DOI: 10.1021/jo051793g (free Supporting Information)


Abstract

Oxidation of alkynes to α-dicarbonyl derivatives through a convenient one-pot procedure via a Brønsted acid-promoted "hydration" and a DMSO-based oxidation sequence has been achieved in high yields.

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proposed mechanism



Key Words

1,2-Diketones, Formic Acid, DMSO


ID: J42-Y2006-200