Copper-Catalyzed Aerobic Intramolecular Dehydrogenative Cyclization of N,N-Disubstituted Hydrazones through Csp3-H Functionalization

被引：68
|
作者：
Zhang, Guangwu [1 ]
Zhao, Yan [1 ]
Ge, Haibo [1 ]
机构：
[1] Indiana Univ Purdue Univ, Dept Chem & Chem Biol, Indianapolis, IN 46202 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 09期
关键词：
C-H activation; copper; cyclization; heterocycles; oxygen; H BOND FUNCTIONALIZATION; COUPLING REACTIONS; TRANSITION-METAL; MOLECULAR-OXYGEN; TERMINAL ALKYNES; C-C; OXIDATIVE ALKYLATION; GLYCINE DERIVATIVES; MONOAMINE-OXIDASE; NITROGEN ATOM;
D O I：
10.1002/anie.201209618
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
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. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：2559 / 2563
页数：5
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