33. BBDFA: A Practical Reagent for Trifluoromethylation of Allylic and Benzylic Alcohols on Preparative Scale

Organofluorine MethodologyDecarboxylative and Deoxygenative Fluoroalkylation CouplingSynthetic Organic MethodologyPre 2020
Written By Altmaniacs
 
 

Han, C.;* Alabanza, L. M.; Kelly, S. M.; Orsi, D. L.; Gosselin, F.; Altman, R. A.*

Org. Proc. Res. Dev. 2019, 23, 1695–1702.

We report a safe and readily prepared reagent [1,1′-biphenyl]-4-yl 2-bromo-2,2-difluoroacetate (BBDFA) for Cu-catalyzed trifluoromethylation of allylic or benzylic alcohols. An operationally simple and column-chromatography-free process to prepare BBDFA was developed and demonstrated on >100 g scale. Detailed reaction calorimetry and thermal analysis of the deoxytrifluoromethylation were performed using cinnamyl alcohol as a model substrate, demonstrating that the reactions could be safely implemented on preparative scale.

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32. Organocatalytic Strategy for Hydrophenolation of gem-Difluoroalkenes