Bromopalladation Triggering the Cascade Oxidative Heterocyclization Reaction of Alkynes with Alkenes in Ionic Liquids

被引：5

作者：

An, Yanni ^{[1
]}

Li, Jianxiao ^{[1
]}

Zhang, Zhenming ^{[1
]}

Li, Chunsheng ^{[1
]}

Yang, Shaorong ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 36卷 / 09期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

palladium-catalyzed; ionic liquids; alkynes; alkenes; heterocycles; CATALYZED INTERMOLECULAR CARBOESTERIFICATION; METHYLENE-GAMMA-LACTONES; STEREOSELECTIVE-SYNTHESIS; ANNULATION; NUCLEOPALLADATION; CHLOROPALLADATION; STRATEGY; ACIDS;

D O I：

10.6023/cjoc201603043

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and practical palladium-catalyzed cascade oxidative heterocyclization has been developed to afford functionalized oxygen-containing five-membered heterocycles in moderate to good yields with high regio- and diastereo-electivities. Their structures were confirmed by IR, H-1 NMR, (13) C NMR and HRMS. Furthermore, the current methodology could also be conveniently applied to the synthesis of naturally occurring biologically active functionalized tetrahydrofurans and gamma-lactones frameworks.

引用

页码：2136 / 2141

页数：6

共 38 条

[1] Palladium-catalyzed cyclization/Heck- and cyclization/conjugate-addition-type sequences in the preparation of polysubstituted furans [J].

Aurrecoechea, Jose M. ;

Durana, Aritz ;

Perez, Elena .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (09) :3650-3653

[2]

Branco LC, 2002, CHEM-EUR J, V8, P3671, DOI 10.1002/1521-3765(20020816)8:16<3671::AID-CHEM3671>3.0.CO

[3]

2-9

[4] Formal [4+1] Annulation Reactions in the Synthesis of Carbocyclic and Heterocyclic Systems [J].

Chen, Jia-Rong ;

Hu, Xiao-Qiang ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

CHEMICAL REVIEWS, 2015, 115 (11) :5301-5365

[5] ent-labdane diterpenoid lactone stereoisomers from Andrographis paniculata [J].

Chen, Lixia ;

Zhu, Huajie ;

Wang, Rui ;

Zhou, Kailan ;

Jing, Yongkui ;

Qiu, Feng .

JOURNAL OF NATURAL PRODUCTS, 2008, 71 (05) :852-855

[6] Arylglyoxals in Synthesis of Heterocyclic Compounds [J].

Eftekhari-Sis, Bagher ;

Zirak, Maryam ;

Akbari, Ali .

CHEMICAL REVIEWS, 2013, 113 (05) :2958-3043

[7] Transition metal-catalyzed C-H functionalization of N-oxyenamine internal oxidants [J].

Huang, Huawen ;

Ji, Xiaochen ;

Wu, Wanqing ;

Jiang, Huanfeng .

CHEMICAL SOCIETY REVIEWS, 2015, 44 (05) :1155-1171

[8] A cascade approach to fused indolizinones through Lewis acid-copper(I) relay catalysis [J].

Huang, Huawen ;

Ji, Xiaochen ;

Wu, Wanqing ;

Jiang, Huanfeng .

CHEMICAL COMMUNICATIONS, 2013, 49 (32) :3351-3353

[9] Nucleopalladation-Initiated Oxyalkenylation of Alkenes: A Strategy To Construct Functionalized Oxygenated Heterocycles [J].

Huang, Liangbin ;

Wang, Qian ;

Wu, Wanqing ;

Jiang, Huanfeng .

JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (16) :7734-7739

[10] Switch of Selectivity in the Synthesis of α-Methylene-γ-Lactones: Palladium-Catalyzed Intermolecular Carboesterification of Alkenes with Alkynes [J].

Huang, Liangbin ;

Wang, Qian ;

Liu, Xiaohang ;

Jiang, Huanfeng .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (23) :5696-5700

← 1 2 3 4 →