Catalytic Oxidative Carbene Coupling of α-Diazo Carbonyls for the Synthesis of β-Amino Ketones via C(sp3)–H Functionalization

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• 作者：Tian-Shu Zhang ; Wen-Juan Hao ; Nan-Nan Wang ; Guigen Li ; Dong-Fang Jiang ; Shu-Jiang Tu ; Bo Jiang
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：18
• 期：13
• 页码：3078-3081
• 全文大小：367K
• 年卷期：0
• ISSN：1523-7052

文摘

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(sp³)–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.