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We report a fluoride-initiated coupling reaction between trifluoromethylarenes and allylsilanes to access allylated α,α-difluorobenzylic compounds. This method's utility is demonstrated through a 30 mmol scale reaction, a sequential allylation/derivatization protocol and multiple examples of site-selective trifluoromethylarene allylation. Initial mechanistic studies suggest a base-induced single electron transfer pathway is responsible for the high efficiency and selectivity of this novel C-F substitution process.
Luo et al. (2019) studied this question.