Synthesis of aryl(difluoromethylenephosphonates) via electrophilic fluorination of α-carbanions of benzylic phosphonates with N- fluorobenzenesulfonimide.

Article abstract of DOI:10.1016/S0040-4020(97)10395-7

The electrophilic fluorination of a wide variety of benzylic phosphonates with N-fluorobenzenesulfonimide has been examined. The fluorination reaction proceeds well in the presence of an array of functional groups such as nitro, bromo, ketone, ester, phenyl and ether groups. Phenyl and biphenyl derivatives containing two α,α-difluoromethylenephosphonate groups can also be prepared. This procedure is compatible with methyl or ethyl phosphonate esters but not with t-butyl esters or with benzylic phosphonates containing an additional benzylic moiety at the para-position.