Copper-Catalyzed aerobic intramolecular dehydrogenative cyclization of n,n-disubstituted hydrazones through C sp 3 -H functionalization

Guangwu Zhang, Yan Zhao, Haibo Ge

Research output: Contribution to journalArticle

57 Scopus citations

Abstract

An aerobic activity: The title reaction proceeds through an oxidation/cyclization/aromatization sequence under an atmosphere of O 2 (see scheme; DBU=1,8-diazabicyclo[5.4.0]undec-7-ene, DCE=1,2-dichloroethane, DMS=dimethylsulfide). This coupling reaction is the first to proceed via an iminium intermediate for a C sp 3-H bond- functionalization process, and provides an environmentally friendly and atom-efficient access to substituted pyrazoles.

Original languageEnglish
Pages (from-to)2559-2563
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number9
DOIs
StatePublished - Feb 25 2013

Keywords

  • C-H activation
  • copper
  • cyclization
  • heterocycles
  • oxygen

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