Ruthenium(II)/N-Heterocyclic Carbene Catalyzed [3+2] Carbocyclization with Aromatic NH Ketimines and Internal Alkynes

被引：123

作者：

Zhang, Jing ^{[1
]}

Ugrinov, Angel ^{[1
]}

Zhao, Pinjing ^{[1
]}

机构：

[1] N Dakota State Univ, Dept Chem & Biochem, Fargo, ND 58108 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 26期

关键词：

CH activation; indenamine; NH ketimines; N-heterocyclic carbenes; ruthenium; H BOND ACTIVATION; CARBON-HYDROGEN BONDS; C-H; ROOM-TEMPERATURE; HETEROCYCLIC CARBENES; BENZOPHENONE IMINE; ARYL CHLORIDES; RUTHENIUM; COMPLEXES; ANNULATION;

D O I：

10.1002/anie.201209031

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Convenient and highly efficient: Indenamines were synthesized using the title reaction, which occurs at ambient temperature, in the absence of oxidants or other metal salts, and in nonpolar solvents. A proposed mechanism involves imine-directed activation of an aromatic C-H bond, alkyne insertion, and carbocyclization by intramolecular imine insertion into Ru-alkenyl linkages. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：6681 / 6684

页数：4

共 67 条

[51] EFFICIENT CATALYTIC ADDITION OF AROMATIC CARBON-HYDROGEN BONDS TO OLEFINS [J].

MURAI, S ;

KAKIUCHI, F ;

SEKINE, S ;

TANAKA, Y ;

KAMATANI, A ;

SONODA, M ;

CHATANI, N .

NATURE, 1993, 366 (6455) :529-531

[52]

Muralirajan K., 2011, ANGEW CHEM, V123, P4255

[53]

Nolan S P., 2006, N HETEROCYCLIC CARBE

[54] Diverse Strategies toward Indenol and Fulvene Derivatives: Rh-Catalyzed C-H Activation of Aryl Ketones Followed by Coupling with Internal Alkynes [J].

Patureau, Frederic W. ;

Besset, Tatiana ;

Kuhl, Nadine ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (07) :2154-2156

[55] Rh(III)-Catalyzed Directed C-H Olefination Using an Oxidizing Directing Group: Mild, Efficient, and Versatile [J].

Rakshit, Souvik ;

Grohmann, Christoph ;

Besset, Tatiana ;

Glorius, Frank .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (08) :2350-2353

[56] C-C, C-O and C-N bond formation via rhodium(III)-catalyzed oxidative C-H activation [J].

Song, Guoyong ;

Wang, Fen ;

Li, Xingwei .

CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) :3651-3678

[57] Rhodium(III)-Catalyzed Arene and Alkene C-H Bond Functionalization Leading to Indoles and Pyrroles [J].

Stuart, David R. ;

Alsabeh, Pamela ;

Kuhn, Michelle ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (51) :18326-18339

[58] Direct C-H Transformation via Iron Catalysis [J].

Sun, Chang-Liang ;

Li, Bi-Jie ;

Shi, Zhang-Jie .

CHEMICAL REVIEWS, 2011, 111 (03) :1293-1314

[59] Tertiary Carbinamine Synthesis by Rhodium-Catalyzed [3+2] Annulation of N-Unsubstituted Aromatic Ketimines and Alkynes [J].

Sun, Zhong-Ming ;

Chen, Shuo-Ping ;

Zhao, Pinjing .

CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (08) :2619-2627

[60]

Tran D. N., 2011, ANGEW CHEM, V123, P11294

← 1 2 3 4 5 6 7 →