Catalytic Oxidative Carbene Coupling of alpha-Diazo Carbonyls for the Synthesis of beta-Amino Ketones via C(sp(3))-H Functionalization

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

Research output: Contribution to journalArticle

Abstract

A catalytic domino oxidative carbene coupling (OCC) of alpha-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 alpha-diazo carbonyls and provides practical access to alpha-(acyloxy)-beta-amino ketones and alpha,beta-diamino ketones.
Original languageEnglish
Pages (from-to)3078-3081
JournalOrganic Letters
StatePublished - Jul 2016

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