Catalytic oxidative  carbene coupling of α-diazo carbonyls  for the synthesis of β-aminoketones  via C(sp3)−H functionalization

          Tian-Shu Zhang,  Wen-Juan Hao, Nan-Nan Wang, Guigen Li,* Dong-Fang Jiang, Shu-Jiang Tu*, and Bo  Jiang*

A catalytic domino oxidative carbene coupling (OCC) of α-diazo carbonyls has been established by treatment with N,N-dimethylanilinesand carboxylic acids (or N-methylaniline) via direct C(sp3)−H functionalization under convenient conditions. The reaction pathway is proposed toproceed through the sequence of carbene formation, enolization, and nucleophilic addition. The reaction enables de-diazotized carbo-oxygenationand carbo-amination of α-diazo carbonyls and provides practical access to α-(acyloxy)-β-amino ketones and α,β-diamino ketones.

  Org. Lett. 2016, 18, 3078-3081