Palladium-catalyzed cyanation of aryl halides with in situ generated CN− from ClCF2H and NaNH2

Abstract

An efficient Pd-catalyzed cyanation of aryl halides with in situ generated CN⁻ anions is described. The CN⁻ source stems from the quadruple cleavage of chlorodifluoromethane (ClCF₂H) with sodium amide (NaNH₂). This transformation features no requirement of a toxic CN source and avoids the problem of HCN generation associated with traditional methods. A series of aryl nitriles are obtained from aryl halides in good yields under mild reaction conditions.