Abstract
Reactions involving the conversion of a benzylic alcohol into a benzylic fluoride using RSF 3 reagents are notoriously difficult to achieve with high stereochemical inversion (S N2 reaction) due to competing dissociative S N1 reaction processes. This Letter develops the methodology of Bio et al., and reports that the addition of a preformed 1:TMS-amine 1:RSF 3 (fluorination reagent) complex as the reagent in these reactions significantly suppresses the S N1 process and promotes a highly stereospecific reaction generating benzylic fluorination products of high %ee.
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