Mondal Soumya, Das Suman, Mondal Subal, Midya Siba P, Ghosh Pradyut
School of Chemical Sciences, Indian Association for the Cultivation of Science, 2A & 2B Raja S. C. Mullick Road, Kolkata 700032, West Bengal, India.
Department of Chemistry, Jadavpur University, 188 Raja S. C. Mullick Road, Kolkata 700032, India.
J Org Chem. 2024 Nov 15;89(22):16750-16758. doi: 10.1021/acs.joc.4c02036. Epub 2024 Nov 4.
An unprecedented oxidative decarboxylative chemical domain of α,β-unsaturated acids and amines for C-N cross-coupled α-ketoamidation is disclosed. Molecular oxygen as a source oxygen in amide and water oxygen in the ketone segment furnished a green and sustainable synthesis of α-ketoamide from feedstock acids and amines. Mechanistically, photocatalyst travels with reductive quenching cycle, whereas pallado-cycle proceeded through oxidative C-N bond formation. Broad substrate scope, functional group tolerance, and CO and HO as traceless byproducts make the present methodology more efficient and attractive.
公开了一种用于C-N交叉偶联α-酮酰胺化反应的前所未有的α,β-不饱和酸和胺的氧化脱羧化学领域。酰胺中的分子氧作为氧源以及酮片段中的水氧,实现了从原料酸和胺出发绿色可持续地合成α-酮酰胺。从机理上讲,光催化剂通过还原猝灭循环运行,而钯循环则通过氧化C-N键形成进行。广泛的底物范围、官能团耐受性以及一氧化碳和水作为无痕副产物,使得本方法更高效且具有吸引力。