Combination of gold and iridium catalysts for the synthesis of N-alkylated amides from nitriles and alcohols

Abstract

An alternative and efficient approach for the synthesis of N-alkylated amides from nitriles and alcohols was proposed and accomplished. By the combination of [(IPr)Au(NTf₂)] (IPr = 1,3-bis(diisopropylphenyl)imidazol-2-ylidene) and [Cp*IrCl₂]₂ (Cp* = η⁵-pentamethylcyclopentadienyl), a series of nitriles were first hydrated to give amides, in which the resulting amides were further N-alkylated with a variety of alcohols as alkylating agents to afford N-alkylated amides with good to excellent yields. Compared with previous methods for the synthesis of N-alkylated amides from nitriles and alcohols as starting materials, this protocol could be accomplished with high atom economy under more environmentally benign conditions.