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 › peer-review

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

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.",

keywords = "C-H activation, copper, cyclization, heterocycles, oxygen",

author = "Guangwu Zhang and Yan Zhao and Haibo Ge",

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T1 - Copper-Catalyzed aerobic intramolecular dehydrogenative cyclization of n,n-disubstituted hydrazones through C sp 3 -H functionalization

AU - Zhang, Guangwu

AU - Zhao, Yan

AU - Ge, Haibo

PY - 2013/2/25

Y1 - 2013/2/25

N2 - 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.

AB - 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.

KW - C-H activation

KW - copper

KW - cyclization

KW - heterocycles

KW - oxygen

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U2 - 10.1002/anie.201209618

DO - 10.1002/anie.201209618

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 9

ER -

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

Abstract

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