Rhodium(III)-Catalyzed Oxidative C-H/C-H Cross-Coupling of Heteroarenes and Masked Benzylamines

被引:30
作者
Hu, Jundie [1 ]
Li, Guobao [1 ]
Yuan, Chunchen [1 ]
Huang, Zhi-Bin [1 ]
Shi, Da-Qing [1 ]
Zhao, Yingsheng [1 ]
机构
[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China
基金
中国国家自然科学基金;
关键词
CARBOXYLIC-ACIDS; DEHYDROGENATIVE HETEROARYLATION; SOLAR-CELLS; THIOPHENES; 1,3-AZOLES; ACCESS; DERIVATIVES; SEMICONDUCTORS; HETEROCYCLES; PYRIDINES;
D O I
10.1021/acs.orglett.6b02773
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first example of oxidative C-H/C-H cross coupling of oxalyl amide-protected benzylamines and various heteroarenes in the presence of a rhodium(III) catalyst has been developed. The route provides a means of synthesizing ortho-heteroarylated benzylamines. The methodology presents broad substrate scope, great functional group tolerance, and good to excellent yields in the synthesis of substituted benzylamines. The study also reveals that the thienoisoquinoline derivatives can be accessed through the intramolecular amination of thiophenyl-substituted benzylamines with palladium(II).
引用
收藏
页码:5998 / 6001
页数:4
相关论文
共 56 条
[41]  
Shinoda M., 2005, U.S. Patent, Patent No. [6,884,821, 6884821]
[42]   Solution-Processable Low-Molecular Weight Extended Arylacetylenes: Versatile p-Type Semiconductors for Field-Effect Transistors and Bulk Heterojunction Solar Cells [J].
Silvestri, Fabio ;
Marrocchi, Assunta ;
Seri, Mirko ;
Kim, Choongik ;
Marks, Tobin J. ;
Facchetti, Antonio ;
Taticchi, Aldo .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) :6108-6123
[43]   Elements of regiocontrol in palladium-catalyzed oxidative arene cross-coupling [J].
Stuart, David R. ;
Villemure, Elisia ;
Fagnou, Keith .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (40) :12072-+
[44]   Cobalt-Catalyzed Oxidative C-H/C-H Cross-Coupling between Two Heteroarenes [J].
Tan, Guangying ;
He, Shuang ;
Huang, Xiaolei ;
Liao, Xingrong ;
Cheng, Yangyang ;
You, Jingsong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (35) :10414-10418
[45]   Charge Mobility and Recombination in a New Hole Transporting Polymer and Its Photovoltaic Blend [J].
Tan, Mein Jin ;
Goh, Wei-Peng ;
Li, Jun ;
Pundir, Gaurav ;
Chellappan, Vijila ;
Chen, Zhi-Kuan .
ACS APPLIED MATERIALS & INTERFACES, 2010, 2 (05) :1414-1420
[46]  
Van Rompaey P., 2007, Patent No. [WO2007042321, 2007042321]
[47]   Oxalyl amide assisted palladium-catalyzed synthesis of pyrrolidones via carbonylation of γ-C(sp3)-H bonds of aliphatic amine substrates [J].
Wang, Chao ;
Zhang, Li ;
Chen, Changpeng ;
Han, Jian ;
Yao, Yingming ;
Zhao, Yingsheng .
CHEMICAL SCIENCE, 2015, 6 (08) :4610-4614
[48]   Easily Accessible Auxiliary for Palladium-Catalyzed Intramolecular Amination of C(sp2)-H and C(sp3)-H Bonds at δ- and ε-Positions [J].
Wang, Chao ;
Chen, Changpeng ;
Zhang, Jingyu ;
Han, Jian ;
Wang, Qian ;
Guo, Kun ;
Liu, Pei ;
Guan, Mingyu ;
Yao, Yingming ;
Zhao, Yingsheng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) :9884-9888
[49]   Highly site-selective sequential alkenylation of oxalyl amide protected phenylpropylamine derivatives via a seven-membered palladacycle [J].
Wang, Qian ;
Han, Jian ;
Wang, Chao ;
Zhang, Jingyu ;
Huang, Zhibin ;
Shi, Daqing ;
Zhao, Yingsheng .
CHEMICAL SCIENCE, 2014, 5 (12) :4962-4967
[50]   Palladium-Catalyzed Oxidative C-H/C-H Cross-Coupling of Indoles and Pyrroles with Heteroarenes [J].
Wang, Zhen ;
Li, Kaizhi ;
Zhao, Dongbing ;
Lan, Jingbo ;
You, Jingsong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (23) :5365-5369