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

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 32期

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

页码：9415 / 9419

页数：5

共 100 条

[31] Manganese- Catalyzed Dehydrogenative [4+2] Annulation of N-H Imines and Alkynes by C- H/N- H Activation** [J].

He, Ruoyu ;

Huang, Zhi-Tang ;

Zheng, Qi-Yu ;

Wang, Congyang .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (19) :4950-4953

[32] Manganese-catalyzed bicyclic annulations of imines and α,β-unsaturated esters via C-H activation [J].

Hu, Yuanyuan ;

Wang, Congyang .

SCIENCE CHINA-CHEMISTRY, 2016, 59 (10) :1301-1305

[33] Cleavage of C-C and C-Si σ-Bonds and Their Intramolecular Exchange [J].

Ishida, Naoki ;

Ikemoto, Wataru ;

Murakami, Masahiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (16) :5912-5915

[34] Rhodium-Catalyzed Ring Opening of Benzocyclobutenols with Site-Selectivity Complementary to Thermal Ring Opening [J].

Ishida, Naoki ;

Sawano, Shota ;

Masuda, Yusuke ;

Murakami, Masahiro .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) :17502-17504

[35]

Ko HM, 2014, NAT CHEM, V6, P739, DOI [10.1038/NCHEM.1989, 10.1038/nchem.1989]

[36] Ruthenium-catalyzed hydroarylations of methylenecyclopropanes: Mild C-H bond functional izations with conservation of cyclopropane rings [J].

Kozhushkov, Sergei I. ;

Yufit, Dmitry S. ;

Ackermann, Lutz .

ORGANIC LETTERS, 2008, 10 (16) :3409-3412

[37] Direct Conversion of Carbon-Hydrogen into Carbon-Carbon Bonds by First-Row Transition-Metal Catalysis [J].

Kulkarni, Amol A. ;

Daugulis, Olafs .

SYNTHESIS-STUTTGART, 2009, (24) :4087-4109

[38] Manganese-catalyzed insertion of aldehydes into a C-H bond [J].

Kuninobu, Yoichiro ;

Nishina, Yuta ;

Takeuchi, Takahiro ;

Takai, Kazuhiko .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (34) :6518-6520

[39] Transition metal-mediated cycloaddition reactions [J].

Lautens, M ;

Klute, W ;

Tam, W .

CHEMICAL REVIEWS, 1996, 96 (01) :49-92

[40] Catalyst-Guided C=Het Hydroarylations by Manganese-Catalyzed Additive-Free C - H Activation [J].

Liang, Yu-Feng ;

Massignan, Leonardo ;

Liu, Weiping ;

Ackermann, Lutz .

CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (42) :14856-14859

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