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Catalytic One-Step Deoxytrifluoromethylation of Alcohols

Francisco de Azambuja, Sydney M. Lovrien, Patrick Ross, Brett R. Ambler, Ryan A. Altman*

*Department of Medicinal Chemistry, The University of Kansas, Lawrence, Kansas 66045, United States, Email: raaltmanku.edu

F. de Azambuja, S. M. Lovrien, P. Ross, B. R. Amber, R. A. Altman, J. Org. Chem., 2019, 84, 2061-2071.

DOI: 10.1021/acs.joc.8b03072 (free Supporting Information)



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Abstract

Phenyl bromodifluoroacetate as bench-stable trifluoromethylation reagent converts readily available alcohols to trifluoromethanes in a Cu-catalyzed deoxytrifluoromethylation reaction. This reaction should be useful for a variety of medicinal, agricultural, and materials chemists.

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proposed mechanism



Copper-Catalyzed Decarboxylative Trifluoromethylation of Allylic Bromodifluoroacetates

B. R. Ambler, R. A. Altman, Org. Lett., 2013, 15, 5578-5581.

Ligand-Controlled Regioselective Copper-Catalyzed Trifluoromethylation To Generate (Trifluoromethyl)allenes

B. R. Ambler, S. Peddi, R. A. Altman, Org. Lett., 2015, 17, 2506-2509.


Key Words

allylic trifluoromethanes, trifluoromethyl alkenes, allenes


ID: J42-Y2019