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Trialkylphosphine-Mediated Synthesis of 2-Acyl Furans from Ynenones

Chao Xu, Stéphane Wittmann, Manuel Gemander, Venla Ruohonen and J. Stephen Clark*

*WestCHEM, School of Chemistry, Joseph Black Building, University of Glasgow, University Avenue, Glasgow G12 8QQ, United Kingdom, Email: stephen.clarkglasgow.ac.uk

C. Xu, S. Wittmann, M. Gemander, V. Ruohonen, J. S. Clark, Org. Lett., 2017, 19, 3556-3559.

DOI: 10.1021/acs.orglett.7b01533 (free Supporting Information)


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Abstract

2-Acyl furans can be constructed from ynenones via a sequential addition of a trialkylphosphine, 5-exo-dig cyclization to form a furan ring, and oxidation of the resulting phosphonium ylide with molecular oxygen. Many common functional groups are tolerated, and the products are obtained in very good yield under mild conditions.

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proposed mechanism



Key Words

furans, oxygen


ID: J54-Y2017