Nickel-catalyzed C(sp2)-H selenation of imidazo[1,2-α]pyridines with arylboronic acids or alkyl reagents using selenium powder

被引:26
作者
Zhu, Jie [1 ]
Zhu, Wenhui [1 ]
Xie, Ping [2 ]
Pittman, Charles U., Jr. [3 ]
Zhou, Aihua [1 ]
机构
[1] Jiangsu Univ, Pharm Sch, Xuefu Rd 301, Zhenjiang City 212013, Jiangsu, Peoples R China
[2] Jiangsu Univ Lib, Xuefu Rd 301, Zhenjiang City 212013, Jiangsu, Peoples R China
[3] Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA
关键词
Selenium; C-Se bond; Nickel-catalyzed; C-H functionalization; Arylboronic acid; S BOND FORMATION; ELEMENTAL SULFUR; ANTIOXIDANT ACTIVITY; PEROXIDASE-ACTIVITY; POTENT ACTIVITY; DISELENIDES; ARYL; ORGANOSELENIUM; CHALCOGENATION; SOLVENT;
D O I
10.1016/j.tet.2018.09.037
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and efficient Ni-catalyzed aryl- and alkyl-selenation of imidazo[1,2-alpha]pyridines employing selenium powder has been developed for the first time. The significant advantages of this protocol are that it is an inexpensive nickel catalyst and exhibits broad functional-group compatibility and good reaction yields. (C) 2018 Published by Elsevier Ltd.
引用
收藏
页码:6569 / 6576
页数:8
相关论文
共 54 条
[1]   Rhodium-catalyzed reductive coupling of disulfides and diselenides with alkyl halides, using hydrogen as a reducing agent [J].
Ajiki, K ;
Hirano, M ;
Tanaka, K .
ORGANIC LETTERS, 2005, 7 (19) :4193-4195
[2]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[3]   Solvent-Controlled Halo-Selective Selenylation of Aryl Halides Catalyzed by Cu(II) Supported on Al2O3. A General Protocol for the Synthesis of Unsymmetrical Organo Mono- and Bis-Selenides [J].
Chatterjee, Tanmay ;
Ranu, Brindaban C. .
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (14) :7145-7153
[4]   Metal-Free Oxidative Trifluoromethylthiolation of Terminal Alkynes with CF3SiMe3 and Elemental Sulfur [J].
Chen, Chao ;
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (30) :12454-12457
[5]   Organic anion-transporting polypeptides contribute to the hepatic uptake of berberine [J].
Chen, Chen ;
Wu, Zhi-Tao ;
Ma, Lei-Lei ;
Ni, Xuan ;
Lin, Yun-Fei ;
Wang, Le ;
Chen, Ke-Ping ;
Huang, Cheng-Gang ;
Pan, Guoyu .
XENOBIOTICA, 2015, 45 (12) :1138-1146
[6]   Anti-oxidative, anti-secretory and anti-inflammatory activities of the extract from the root bark of Lycium chinense (Cortex Lycii) against gastric ulcer in mice [J].
Chen, Hongxia ;
Olatunji, Opeyemi J. ;
Zhou, Yifeng .
JOURNAL OF NATURAL MEDICINES, 2016, 70 (03) :610-619
[7]   Cu-catalyzed sulfenylation of imidazol[1,2-a]pyridine via C-H functionalization using a combination of Na2S2O3 and halides [J].
Ding, Yingcai ;
Xie, Ping ;
Zhu, Wenhui ;
Xu, Baojun ;
Zhao, Wannian ;
Zhou, Aihua .
RSC ADVANCES, 2016, 6 (85) :81932-81935
[8]   Iron-Facilitated Iodine-Mediated Electrophilic Annulation of N,N-Dimethyl-2-alkynylanilines with Disulfides or Diselenides [J].
Du, Hui-Ai ;
Tang, Ri-Yuan ;
Deng, Chen-Liang ;
Liu, Yan ;
Li, Jin-Heng ;
Zhang, Xing-Guo .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (14-15) :2739-2748
[9]  
EI-Sayed W. M., 2013, EUR J PHARMACOL, V715, P212
[10]   Photo-induced copper-catalyzed C-H chalcogenation of azoles at room temperature [J].
Gandeepan, Parthasarathy ;
Mo, Jiayu ;
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2017, 53 (43) :5906-5909