Rh(III)-Catalyzed Mild Coupling of Nitrones and Azomethine lmines with Alkylidenecyclopropanes via C-H Activation: Facile Access to Bridged Cycles

被引：92

作者：

Bai, Dachang ^{[1
]}

Xu, Teng ^{[1
]}

Ma, Chaorui ^{[1
]}

Zheng, Xin ^{[1
]}

Liu, Bingxian ^{[1
]}

Xie, Fang ^{[2
]}

Li, Xingwei ^{[1
,2
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn, Henan Key Lab Organ Funct Mol & Drug Innovat, Xinxiang 453007, Peoples R China

[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

来源：

ACS CATALYSIS | 2018年 / 8卷 / 05期

关键词：

rhodium(III); alkylidenecyclopropane; nitrone; azomethine imine; dipolar addition; 1,3-DIPOLAR CYCLOADDITION REACTIONS; CARBON-HYDROGEN BONDS; CHEMICAL-TRANSFORMATIONS; ROOM-TEMPERATURE; N-HETEROCYCLES; FUNCTIONALIZATION; ALKENES; ALKYNES; ANNULATION; ARENES;

D O I：

10.1021/acscatal.8b00746

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Bridged cycles are an important class of structural motif in various biologically active molecules. Rh(III)-catalyzed C-H activation of nitrones and azomethine imines in the context of dipolar addition with alkylidenecyclopropanes (ACPs) have been realized. By taking advantage of the ring strain in ACPs, the reaction with aryl nitrones delivered bridged [3.2.1] bicyclic isoxazolidines, and reaction with azomethine imines afforded bridged tricyclic pyrazolones under the same conditions, where both the nitrone and azomethine imine act as a dipolar directing group. All the reactions occurred under mild conditions with broad substrates scope, high efficiency, and >20:1 diastereoselectivity. The synthetic applications of this protocol have also been demonstrated.

引用

页码：4194 / 4200

页数：13

共 50 条

[41] Rh(III)-Catalyzed C-H Activation and Double Directing Group Strategy for the Regioselective Synthesis of Naphthyridinones [J].

Huckins, John R. ;

Bercot, Eric A. ;

Thiel, Oliver R. ;

Hwang, Tsang-Lin ;

Bio, Matthew M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (39) :14492-14495

[42] Rh(III)-Catalyzed C-C Coupling of Diverse Arenes and 4-Acyl-1-sulfonyltriazoles via C-H Activation [J].

Tian, Miaomiao ;

Liu, Bingxian ;

Sun, Jiaqiong ;

Li, Xingwei .

ORGANIC LETTERS, 2018, 20 (16) :4946-4949

[43] 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

[44] Rhodium(III)-Catalyzed Mild Alkylation of (Hetero)Arenes with Cyclopropanols via C-H Activation and Ring Opening [J].

Zhou, Xukai ;

Yu, Songjie ;

Qi, Zisong ;

Kong, Lingheng ;

Li, Xingwei .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11) :4869-4875

[45] Rh(III)-catalyzed C-H activation-desymmetrization of diazabicycles with arenes: facile synthesis of functionalized cyclopentenes [J].

Zhang, Yan ;

Wu, Qifan ;

Cui, Sunliang .

CHEMICAL SCIENCE, 2014, 5 (01) :297-302

[46] An Efficient Method for the Preparation of Styrene Derivatives via Rh(III)-Catalyzed Direct C-H Vinylation [J].

Otley, Kate D. ;

Ellman, Jonathan A. .

ORGANIC LETTERS, 2015, 17 (05) :1332-1335

[47] Complementary Regioselectivity in Rh(III)-Catalyzed Insertions of Potassium Vinyltrifluoroborate via C-H Activation: Preparation and Use of 4-Trifluoroboratotetrahydroisoquinolones [J].

Presset, Marc ;

Oehlrich, Daniel ;

Rombouts, Frederik ;

Molander, Gary A. .

ORGANIC LETTERS, 2013, 15 (07) :1528-1531

[48] Aldehyde as a Traceless Directing Group for Rh(III)-Catalyzed C-H Activation: A Facile Access to Diverse Indolo[1,2-a]quinolines [J].

Liu, Xingyan ;

Li, Xiaoyu ;

Liu, Hu ;

Guo, Qiang ;

Lan, Jingbo ;

Wang, Ruilin ;

You, Jingsong .

ORGANIC LETTERS, 2015, 17 (12) :2936-2939

[49] Diaryliodoniums by Rhodium(III)-Catalyzed C-H Activation: Mild Synthesis and Diversified Functionalizations [J].

Xie, Fang ;

Zhang, Zhipeng ;

Yu, Xinzhang ;

Tang, Guodong ;

Li, Xingwei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (25) :7405-7409

[50] Cooperative Co(III)/Cu(II)-Catalyzed C-N/N-N Coupling of Imidates with Anthranils: Access to 1H-Indazoles via C-H Activation [J].

Li, Lei ;

Wang, He ;

Yu, Songjie ;

Yang, Xifa ;

Li, Xingwei .

ORGANIC LETTERS, 2016, 18 (15) :3662-3665

← 1 2 3 4 5 →