Metal-free electrochemical synthesis of α-ketoamides via decarboxylative coupling of α-keto acids with isocyanides and water

被引:30
作者
Zhao, Feng [1 ]
Meng, Na [2 ]
Sun, Ting [1 ]
Wen, Jiangwei [2 ]
Zhao, Xiaohui [3 ,4 ]
Wei, Wei [2 ,3 ,4 ]
机构
[1] Guizhou Educ Univ, Sch Chem & Mat Sci, Key Lab Funct Organ Mol, Guiyang 550018, Peoples R China
[2] Qufu Normal Univ, Sch Chem & Chem Engn, Qufu 273165, Peoples R China
[3] Northwest Inst Plateau Biol, Qinghai Prov Key Lab Tibetan Med Res, Xining 810008, Qinghai, Peoples R China
[4] Northwest Inst Plateau Biol, CAS Key Lab Tibetan Med Res, Xining 810008, Qinghai, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2021年 / 8卷 / 23期
关键词
ONE-POT SYNTHESIS; OXOCARBOXYLIC ACIDS; TERMINAL ALKYNES; OXIDATIVE AMIDATION; PROTEASE INHIBITOR; GENERAL-APPROACH; METHYL KETONES; FACILE ACCESS; C-H; ACYLATION;
D O I
10.1039/d1qo01351c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild and environmentally benign electrochemical strategy has been developed for the synthesis of alpha-ketoamides via a decarboxylative coupling reaction of alpha-keto acids with isocyanides and water. The present reaction was efficiently conducted under constant current electrolysis using n-Bu4NI as the electrolyte in an undivided cell. A series of alpha-ketoamides could be conveniently and rapidly constructed at room temperature in the absence of transition metal catalysts and external oxidants. Mechanistic studies suggested that water not only served as a starting material to construct alpha-ketoamides, but also played an important role in promoting the electrochemical redox of alpha-keto acids.
引用
收藏
页码:6508 / 6514
页数:7
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