Catalytic Oxidative Carbene Coupling of α-Diazo Carbonyls for the Synthesis of β-Amino Ketones via C(sp(3))-H Functionalization.
A catalytic domino oxidative carbene coupling (OCC) of α-diazo carbonyls has been established by treatment with N,N-dimethylanilines and carboxylic acids (or N-methylaniline) via direct C(sp(3))-H functionalization under convenient conditions. The reaction pathway is proposed to proceed through the sequence of carbene formation, enolization, and nucleophilic addition. The reaction enables de-diazotized carbo-oxygenation and carbo-amination of α-diazo carbonyls and provides practical access to α-(acyloxy)-β-amino ketones and α,β-diamino ketones.
School of Chemistry and Chemical Engineering, Jiangsu Normal University , Xuzhou 221116, P. R. China.
Tian-Shu
TS
Zhang
School of Chemistry and Chemical Engineering, Jiangsu Normal University , Xuzhou 221116, P. R. China.
Wen-Juan
WJ
Hao
School of Chemistry and Chemical Engineering, Jiangsu Normal University , Xuzhou 221116, P. R. China.
Nan-Nan
NN
Wang
Department of Chemistry and Biochemistry, Texas Tech University , Lubbock, Texas 79409-1061, United States ; and.|Institute of Chemistry & BioMedical Sciences, Collaborative Innovation Center of Chemistry for Life Sciences, Nanjing University , Nanjing 210093, P. R. China.
Guigen
G
Li
School of Chemistry and Chemical Engineering, Jiangsu Normal University , Xuzhou 221116, P. R. China.
Dong-Fang
DF
Jiang
School of Chemistry and Chemical Engineering, Jiangsu Normal University , Xuzhou 221116, P. R. China.
Shu-Jiang
SJ
Tu
School of Chemistry and Chemical Engineering, Jiangsu Normal University , Xuzhou 221116, P. R. China.|Department of Chemistry and Biochemistry, Texas Tech University , Lubbock, Texas 79409-1061, United States ; and.
Bo
B
Jiang