Synthetic Blocks for Organofluorine Compounds : Chemistries of Trifluoroacetimidoyl Halides

Abstract

Preparation and reaction of trifluoroacetimidoyl halides 1 a (X=Cl), b (X=Br), c (X=I) have been summarized. Chemistries of three types of reactive intermediates, trifluoroacetimidoyl carbocations, carbanions and radicals were discussed. Reactions of 1 a with various nucleophiles proceeded smoothly, while palladation, zincation and lithiation of 1 c enabled carbon-carbon bond formation with electrophiles at the imidoyl carbon Meanwhile, photolysis of 1 c provided the corresponding radicals which underwent intramolecular cyclization leading to 2-trifluoromethylindoles.