Selectfluor (F-TEDA-BF4) C7H14B 2ClF9N2

Abstract

(A) Selectfluor is a versatile reagent for fluoroalkylation of alkenes and acetylenes under mild conditions. This reaction follows Markovnikov-type regioselectivity. (B) Selectfluor also helps in the deprotection of PMP, THP, and 1,3-dithiones. Acetonitrile and nitromethane (5% H2O content) can be used as solvent. In the presence of 1.2 equivalents of Selectfluor, deprotection is complete in five hours. (C) Selectfluor acts as a mediator for the introduction of a perfluoroalkyl moiety containing a functional group at the benzylic position in hexamethylbenzene, in the presence of polyfluoroalcohol or potassium salts of perfluoroalkane carboxylic acid. (D) Selectfluor provides one-pot fluorination and anomeric functionalisation of a carbohydrate. In the presence of a nucleophile, it reacts with glycals to give 2-deoxy-2-fluoro derivatives with concurrent introduction of a nucleophile to the anomeric position. (E) Selectfluor can be used as an excellent promoter for allylation of aldehydes and amines with allyltributyltin in one step, to form homoallylic alcohols or amines. (F) Selectfluor allows the green electrophilic fluorination of indole compounds in high chemoselectivity and yield. In the presence of thiols, intermediate sulfides are formed. (G) Selectfluor provides a straightforward route for the synthesis of difluorinated carbonyl compounds upon reaction with enamines under mild conditions. © Georg Thieme Verlag Stuttgart.