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

Guangwu Zhang; Yan Zhao; Haibo Ge

doi:10.1002/anie.201209618

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

Guangwu Zhang, Yan Zhao, Haibo Ge

Chemistry and Biochemistry

Research output: Contribution to journal › Article

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 language	English
Pages (from-to)	2559-2563
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	9
DOIs	https://doi.org/10.1002/anie.201209618
State	Published - Feb 25 2013

Keywords

C-H activation
copper
cyclization
heterocycles
oxygen

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Zhang, G., Zhao, Y., & Ge, H. (2013). Copper-Catalyzed aerobic intramolecular dehydrogenative cyclization of n,n-disubstituted hydrazones through C sp 3 -H functionalization. Angewandte Chemie - International Edition, 52(9), 2559-2563. https://doi.org/10.1002/anie.201209618

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