Organic Chemistry Portal

Abstracts

Search:

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


see article for more reactions

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.

see article for more examples


proposed mechanism



Key Words

furans, oxygen


ID: J54-Y2017