TY - JOUR
T1 - Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation
AU - Seo, Hong Ahn
AU - Cho, Yeon Ho
AU - Lee, Ye Sol
AU - Cheon, Cheol-Hong
PY - 2015/11/18
Y1 - 2015/11/18
N2 - 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.
AB - 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.
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U2 - 10.1021/acs.joc.5b01922
DO - 10.1021/acs.joc.5b01922
M3 - Article
AN - SCOPUS:84952838276
VL - 80
SP - 11993
EP - 11998
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 24
ER -