Wang Xiao-Fei, Yu Shu-Sheng, Wang Chao, Xue Dong, Xiao Jianliang
Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, 710062, P. R. China.
Org Biomol Chem. 2016 Aug 7;14(29):7028-37. doi: 10.1039/c6ob00736h. Epub 2016 Jul 1.
A novel and efficient protocol for the synthesis of amides is reported which employs a BODIPY catalyzed oxidative amidation reaction between aromatic aldehydes and amines under visible light. Compared with the known Ru or Ir molecular catalysts and other organic dyes, the BODIPY catalyst showed higher reactivity toward this reaction. Mechanistic studies reveal that dioxygen could be activated through an ET and a SET pathway, forming active peroxides in situ, which are vital for the key step of the reaction, i.e. the oxidation of hemiaminal to amide. The broad substrate scope and mild reaction conditions make this reaction practically useful and environmentally friendly for the synthesis of amide compounds.
报道了一种新颖且高效的酰胺合成方法,该方法采用硼二吡咯(BODIPY)催化芳族醛与胺在可见光下发生氧化酰胺化反应。与已知的钌或铱分子催化剂及其他有机染料相比,BODIPY催化剂对该反应表现出更高的反应活性。机理研究表明,氧气可通过电子转移(ET)和单电子转移(SET)途径被活化,原位形成活性过氧化物,这对于反应的关键步骤,即半胺氧化为酰胺至关重要。广泛的底物范围和温和的反应条件使得该反应在酰胺化合物的合成中具有实际应用价值且环境友好。