Stereoselective Monofluoromethylation of Primary and Secondary Alcohols by Using a Fluorocarbon Nucleophile in a Mitsunobu Reaction

Abstract

OH is exchanged: An efficient Mitsunobu reaction that uses a fluorinated carbon pronucleophile for the facile synthesis of monofluoromethyl derivatives of alcohols is reported (see scheme; DIAD=diisopropyl azodicarboxylate). This reaction can be performed under mild conditions and is highly feasible for primary, secondary, allylic, benzylic, and alicyclic alcohols. Excellent enantiospecificity is observed for chiral alcohols.