SynOpen (Jun 2022)
Microwave-Assisted, Metal-Free, Chemoselective N-Formylation of Amines using 2-Formyl-1,3-dimethyl-1H-imidazol-3-ium Iodide and In Situ Synthesis of Benzimidazole and Isocyanides
Abstract
An efficient, environmentally benign, chemoselective, microwave-assisted N-formylation protocol of aromatic, aliphatic, alicyclic, benzylic amines, inactivated aromatic amines and sterically demanding heterocyclic amines using 2-formyl-1,3-dimethyl-1H-imidazol-3-ium iodide has been developed. This affords a series of N-substituted formamides with good to excellent yields (23 examples, 53–96% yield) and can be readily scaled. The methodology can be further extended to synthesize benzimidazole and isocyanide derivatives.
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