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Methylenation of Perfluoroalkyl Ketones using a Peterson Olefination Approach

Trevor A. Hamlin, Christopher B. Kelly, Robin M. Cywar and Nicholas E. Leadbeater*

*Department of Chemistry, University of Connecticut, 55 North Eagleville Road, Storrs, Connecticut 06269-3060, United States, Email: nicholas.leadbeateruconn.edu

T. A. Hamlin, C. B. Kelly, R. M. Cywar, N. E. Leadbeater, J. Org. Chem., 2014, 79, 1145-1155.

DOI: 10.1021/jo402577n (free Supporting Information)


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Abstract

An operationally simple, inexpensive, and rapid route for the olefination of a wide array of trifluoromethyl ketones using a Peterson olefination approach gives very good yields of 3,3,3-trifluoromethylpropene products and can be performed without purification of the β-hydroxysilyl intermediate. The reaction can be extended to other perfluoroalkyl substituents and is easily scaled up.

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Key Words

Peterson Olefination, trifluoromethyl alkenes


ID: J42-Y2014