Science of Synthesis

Champagne, P. A.; Drouin, M.; Paquin, J.-F., Science of Synthesis Knowledge Updates, (2016) 1, 419.

General Introduction

Benzylic fluorides have received a lot of attention recently as a novel fluorinated motif with potential interest in different spheres of chemistry. The new developments in their synthesis now enable researchers to generate a wide variety of benzylic fluorides, with structures from the simplest to the most complex derivatives of bioactive compounds. Traditional synthetic methods, such as nucleophilic substitution at benzylic leaving groups or deoxofluorination, were described in the original Section 34.6, and only more-recent progress will be presented herein. Important new methodologies include C—H functionalizations, fluorinative additions onto vinylarenes, fluorodecarboxylations, and updated deoxofluorination protocols. When reported, emphasis will be put on enantioselective transformations for the synthesis of chiral benzylic fluorides.