Useful Fluorine-Containing Building Block

Trifluoro-N-phenylacetimidoyl chloride (1) has been widely used as a useful fluorine-containing building block for synthesis of many compounds. The chlorine attached to the imidoyl carbon of 1 can easily be replaced by various nucleophiles such as alcohols,¹⁾ amines,²⁾ and carbanions.³⁾ The nucleophilic benzylation product, prepared from benzyl alchohol, is a reagent for O-benzylation.⁴⁾ The glycosylation products of 1 are used as effective glycosyl donors.⁵⁾ Reductive C-F and C-Cl bond cleavage reactions of 1 afford a gem-difluorinated dianion equivalent, which can give a variety of difluorinated imines.⁶⁾ Trifluoromethylated vinyl metals, metal-halogen exchange products of 1, are used for the design of many synthetic compounds.⁷⁾