Copper-Catalyzed 8-Aminoquinoline-Directed Selenylation of Arene and Heteroarene C-H Bonds

被引:102
作者
Mandal, Anup [1 ]
Sahoo, Harekrishna [1 ]
Baidya, Mahiuddin [1 ]
机构
[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India
关键词
DISELENIDES; THIOLATION; SELENIUM; ORGANOSELENIUM; SELENATION; CHALCOGENATION; DERIVATIVES; BIDENTATE; CHEMISTRY; SOLVENT;
D O I
10.1021/acs.orglett.6b01420
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient copper-catalyzed/-mediated and 8-aminoquinoline-assisted arylselenylation of inert C-H bonds of (hetero)arenes with readily available diselenides has been reported. The reaction is scalable and tolerates a wide spectrum of functional groups to deliver diarylselenides in very high yields (up to 98%). Application of this methodology to the facile synthesis of thiophene-fused selenochromone was demonstrated.
引用
收藏
页码:3202 / 3205
页数:4
相关论文
共 50 条
[21]   Palladium-Catalyzed Remote δ-C-H Selenylation of Arylethylamide and Alkenylethylamide Derivatives [J].
Ma, Wenbo ;
Zhou, Yunhao ;
Wang, Yang ;
Li, Bo ;
Zheng, Tao ;
Cheng, Zemin ;
Mei, Ruhuai .
ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (20) :3544-3550
[22]   Direct Synthesis of 4-Organylselanylpyrazoles by Copper-Catalyzed One-Pot Cyclocondensation and C-H Bond Selenylation Reactions [J].
Oliveira, Daniela H. ;
Aquino, Thalita B. ;
Nascimento, Jose Edmilson R. ;
Perin, Gelson ;
Jacob, Raquel G. ;
Alves, Diego .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (18) :4041-4049
[23]   Ir(iii)-catalyzed thioether directed arene C-H alkenylation [J].
Li, Chen ;
Chen, Xian ;
Bao, Rui-Peng ;
Li, Dong-Li ;
Zhang, Kun ;
Wang, Dong-Hui .
RSC ADVANCES, 2019, 9 (52) :30134-30138
[24]   Copper-Catalyzed Regioselective Cleavage of C-X and C-H Bonds: A Strategy for Sulfur Dioxide Fixation [J].
Yang, Daoshan ;
Sun, Pengfei ;
Wei, Wei ;
Liu, Fengjuan ;
Zhang, Hui ;
Wang, Hua .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (17) :4423-4427
[25]   Copper-Catalyzed C-H Difluoroalkylation of Coumarins with Fluoroalkyl Bromides [J].
Rao, Min ;
Wei, Zhenwei ;
Yuan, Yaofeng ;
Cheng, Jiajia .
CHEMCATCHEM, 2020, 12 (20) :5256-5260
[26]   Copper-catalyzed oxidative C-H/C-H cross-coupling of benzamides and thiophenes [J].
Zhao, Sheng ;
Yuan, Jun ;
Li, Yi-Chen ;
Shi, Bing-Feng .
CHEMICAL COMMUNICATIONS, 2015, 51 (64) :12823-12826
[27]   Copper-catalyzed monoselective C-H amination of ferrocenes with alkylamines [J].
Jia, Zhen-Sheng ;
Yue, Qiang ;
Li, Ya ;
Xu, Xue-Tao ;
Zhang, Kun ;
Shi, Bing-Feng .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2021, 17 :2488-2495
[28]   Copper promoted, directed sulfenylation and phenoxylation of benzamide C-H bonds [J].
Ha, Nguyen Van Vinh ;
Ha, Nguyen Thi Thu ;
Khanh, Ong Ngoc ;
Phuong, Dinh Truc ;
Nhat, Ho Thanh ;
Tung, Nguyen Thanh .
VIETNAM JOURNAL OF CHEMISTRY, 2023, 61 (02) :204-209
[29]   Copper-Catalyzed Direct Arylselenation of Anilines by C-H Bond Cleavage [J].
Ricordi, Vanessa G. ;
Thurow, Samuel ;
Penteado, Filipe ;
Schumacher, Ricardo F. ;
Perin, Gelson ;
Lenardao, Eder J. ;
Alves, Diego .
ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) :933-939
[30]   Copper-Catalyzed Intramolecular Benzylic C-H Amination for the Synthesis of Isoindolinones [J].
Yamamoto, Chiaki ;
Takamatsu, Kazutaka ;
Hirano, Koji ;
Miura, Masahiro .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (17) :7675-7684