Methylenecyclopropane Annulation by Manganese(I)-Catalyzed Stereoselective C-H/C-C Activation

被引:122
作者
Liang, Yu-Feng [1 ]
Mueller, Valentin [1 ]
Liu, Weiping [1 ]
Muench, Annika [2 ]
Stalke, Dietmar [2 ]
Ackermann, Lutz [1 ]
机构
[1] Georg August Univ Gottingen, Inst Organ & Biomol Chem, D-37077 Gottingen, Germany
[2] Georg August Univ Gottingen, Inst Anorgan Chem, D-37077 Gottingen, Germany
基金
欧洲研究理事会;
关键词
C-H activation; heterocycles; imines; manganese; reaction mechanisms; CARBON-CARBON BONDS; CROSS-COUPLING REACTIONS; H ACTIVATION; CATALYZED HYDROARYLATIONS; CARBOXYLATE ASSISTANCE; SITE-SELECTIVITY; COBALT CATALYSIS; HYDROGEN BONDS; MANGANESE; ALKYNES;
D O I
10.1002/anie.201704767
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
C-H/C-C functionalizations with methylenecyclopropanes (MCPs) were accomplished with a versatile base-metal catalyst. A robust manganese(I) complex enabled the expedient annulation of MCPs by synthetically meaningful ketimines to deliver, upon one-pot hydroarylation, densely substituted polycylic anilines in a step-economical fashion. Mechanistic studies provided strong support for a facile organometallic C-H manganation, while typical cobalt, ruthenium, rhodium, and palladium catalysts were found completely ineffective.
引用
收藏
页码:9415 / 9419
页数:5
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