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

[21] Rh(III)-Catalyzed [3+2] Annulation of Aniline Derivatives with Vinylsilanes via C-H Activation/Alkene Cyclization: Access to Highly Regioselective Indoline Derivatives [J].

Khake, Shrikant M. ;

Chatani, Naoto .

ACS CATALYSIS, 2021, 11 (19) :12375-12383

[22] Regio- and Diastereoselective Access to Fused Isoxazolidines via Ru(II)-Catalyzed C-H Activation of Nitrones and Coupling with Perfluoroalkylolefins [J].

Li, Yunyun ;

Xie, Fang ;

Liu, Yuan ;

Yang, Xifa ;

Li, Xingwei .

ORGANIC LETTERS, 2018, 20 (02) :437-440

[23] Rh(III)-Catalyzed intramolecular redox-neutral cyclization of alkenes via C-H activation [J].

Shi, Zhuangzhi ;

Boultadakis-Arapinis, Melissa ;

Koester, Dennis C. ;

Glorius, Frank .

CHEMICAL COMMUNICATIONS, 2014, 50 (20) :2650-2652

[24] Rhodium(III)-Catalyzed Synthesis of Spiropiperidine Derivatives via C-H Activation [J].

Peneau, Augustin ;

Retailleau, Pascal ;

Guillou, Catherine ;

Chabaud, Laurent .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) :2324-2340

[25] Rh(iii)-Catalyzed spiroannulation of ketimines with cyclopropenones via sequential C-H/C-C bond activation [J].

Hu, Hong ;

Li, Bin-Shi ;

Xu, Jing-Lei ;

Sun, Wei ;

Wang, Yong ;

Sun, Meng .

CHEMICAL COMMUNICATIONS, 2022, 58 (30) :4743-4746

[26] Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide [J].

Xu, Shiyang ;

Huang, Baoliang ;

Qiao, Guanyu ;

Huang, Ziyue ;

Zhang, Zhen ;

Li, Zongyang ;

Wang, Peng ;

Zhang, Zhenhua .

ORGANIC LETTERS, 2018, 20 (18) :5578-5582

[27] Aerobic Oxidative C-H Olefination of Arylamides with Unactivated Olefins via a Rh(III)-Catalyzed C-H Activation [J].

Jambu, Subramanian ;

Shambhavi, Chikkabagilu Nagaraju ;

Jeganmohan, Masilamani .

ORGANIC LETTERS, 2021, 23 (08) :2964-2970

[28] Theoretical Investigations on Rh(III)-Catalyzed Cross-Dehydrogenative Aryl-Aryl Coupling via C-H Bond Activation [J].

Zhao, Dan ;

Li, Xiaoxi ;

Han, Keli ;

Li, Xingwei ;

Wang, Yong .

JOURNAL OF PHYSICAL CHEMISTRY A, 2015, 119 (12) :2989-2997

[29] Rh(III)-Catalyzed Enaminone-Directed Alkenyl C-H Activation for the Synthesis of Salicylaldehydes [J].

Qi, Bing ;

Guo, Shan ;

Zhang, Wenjing ;

Yu, Xiaolong ;

Song, Chao ;

Zhu, Jin .

ORGANIC LETTERS, 2018, 20 (13) :3996-3999

[30] Rh(III)-catalyzed 7-azaindole synthesis via C-H activation/annulative coupling of aminopyridines with alkynes [J].

Kim, Yechan ;

Hong, Sungwoo .

CHEMICAL COMMUNICATIONS, 2015, 51 (56) :11202-11205

← 1 2 3 4 5 →