1 - Nucleophilic reactions in the synthesis of organofluorine compounds

Abstract

Nucleophilic fluorinations and fluoroalkylations are widely used for the synthesis of organofluorine compounds. Efficient nucleophilic deoxyfluorination of alcohols and gem-difluorination of carbonyl compounds can be achieved using the commercially available nucleophilic fluorination reagents, such as diethylaminosulfur trifluoride, Deoxo-Fluor, XtalFluor, and FluoLead. Fluoroalkylation reactions, including difluoromethylations and trifluoromethylations, are of unique importance in the design of pharmaceuticals. Enantioselective nucleophilic fluorinations and trifluoromethylations can be achieved using chiral auxiliaries or cinchonidine-based alkaloids as the chiral catalysts. Nucleophilic trifluoromethylations are also used in the efficient synthesis of the pharmaceutically significant trifluoromethoxylated and trifluoromethylthiolated compounds. This chapter outlines modern nucleophilic fluorinations and fluoroalkylation reactions that have broad scope in the design of pharmaceuticals and materials.