Deoxyfluorination of Alcohols with 3,3-Difluoro-1,2-diarylcyclopropenes

Jinbo Hu reports the deoxyfluorination of alcohols with 3,3-difluoro-1,2-diarylcyclopropenes.

Alkyl fluorides constitute a valuable class of organofluorine compounds for pKa modulation, lipophilicity tuning, and selective blocking of oxidative metabolism. Among the fluorination methods developed for their synthesis, the deoxyfluorination of alcohols via in situ activation is a leading approach due to the ready availability of both natural and synthetic alcohols. Known deoxyfluorination reactions mainly rely on ‘S-F’ and ‘N-C-F’ reagents. While these reagents possess features such as high reactivity, good chemoselectivity, enhanced shelf stability, ready availability or low cost, their selective reaction with multiple alcohols is usually paid little attention with apparently sterically controlled selectivity. Moreover, there is still a lack of a deoxyfluorination method that is capable of fluorinating multiple alcohols selectively at the relatively electron-rich position rather than the less sterically hindered position. 

To tackle the existing chemoselectivity problem, the group of Professor Jinbo Hu from the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (P. R. of China) developed a novel strategy for the deoxyfluorination of alcohols based on cyclopropenium cation activation by use of 3,3-difluoro-1,2-diarylcyclopropenes (CpFluors) as easily accessible and reactivity-tunable reagents.

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