A new protocol for the direct formation of amides from imines derived from aromatic aldehydes via metal-free aerobic oxidation in the presence of cyanide is described. This protocol was applicable to various aldimines, and the desired amides were obtained in moderate to good yields. Mechanistic studies suggested that this aerobic oxidative amidation might proceed via the addition of cyanide to imines followed by proton transfer from carbon to nitrogen in the original imines, leading to carbanions of α-amino nitriles, which undergo subsequent oxidation with molecular oxygen in air to provide the desired amide compounds.
Ah ighly efficient protocolf or the synthesis of benzimidazole-substituted arylboronic acids was developed via aerobic oxidative cyclization of 1,2-aryldiamines and formyl-substituted aryl MIDA (N-methyliminodiacetic acid) boronatesu sing potassium iodide as an ucleophilic catalyst. Furthermore,aone-pot protocolf or the synthesiso fb enzimidazole-substituted arylboronic acids from 1,2phenylenediamines and formyl-substituted arylboronic acids was developed without the isolation of any intermediates.T he resulting boronic acids were further subjected to Suzuki-Miyaura coupling reactions without isolation, leading to diaryl-substituted benzimidazoles with only one separation step.
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