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

29 Scopus citations

Abstract

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.

Original languageEnglish
Pages (from-to)3078-3081
Number of pages4
JournalOrganic Letters
Volume18
Issue number13
DOIs
StatePublished - Jul 1 2016

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