摘要
在荧光染料与镍协同催化下,以N-苯甲酰基琥珀酰亚胺类化合物为羰基化试剂,实现了α-氨基酸的脱羧羰基化反应.该反应以较好的收率(最高可达78%)合成了16种含α-氨基酮的衍生物,光转化效率最高可达3.25×10^(-1)mmol/(kW·h).此外,提出了该光催化反应的可能机理:α-氨基羧酸在可见光催化下生成α-氨基烷基自由基,并进入镍催化循环中,经过氧化加成和还原消除过程后生成α-氨基酮类化合物.该反应可以在温和条件下合成不同种类的α-氨基酮类化合物,显示了良好的底物适应性,可能在含有α-氨基酮的药物分子合成及肽的化学修饰等方面具有很广泛的应用价值.
The decarboxylative carbonylation ofα-amino acids was carried out with N-benzoyl succinimide as the carbonylation reagent under the synergistic catalysis of fluorescent dye/nickel catalysts.In this reaction,16 kinds ofα-amino ketone-containing derivatives were synthesized with good yields(up to 78%),and the light conversion efficiency was up to 3.25×10^(-1) mmol/(kW•h).In addition,the possible mechanism of the photocatalytic reaction was proposed:α-amino carboxylic acid was catalyzed by visible light to formα-amino alkyl radicals,which entered the nickel catalytic cycle and producedα-amino ketone target compound via oxidation addition and reduction elimination process.The reactions could generate a variety ofα-amino ketones with broad substrate scope under mild conditions and might have widespread use in synthesis ofα-amino ketone-containing drug molecules and peptide modifications.
作者
余卫国
王灵娜
俞晓聪
罗书平
Yu Weiguo;Wang Lingna;Yu Xiaocong;Luo Shuping(Institute of Medicinal Chemistry,Zhejiang Pharmaceutical Colloge,Ningbo,Zhejiang 315100;State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology,Zhejiang University of Technology,Hangzhou 310014)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2022年第4期1216-1223,共8页
Chinese Journal of Organic Chemistry
基金
浙江省基础公益基金(No.LGG21H300001)
浙江省教育厅科研基金(No.Y201432790)资助项目。
关键词
光催化
镍催化
单电子转移
脱羧偶联反应
photocatalysis
nickel catalysis
single electron transfer
decarboxylative coupling reaction
