Thiol Activation toward Selective Thiolation of Aromatic C-H Bond

被引:39
作者
Wang, Jing-Hao [1 ,2 ]
Lei, Tao [1 ,2 ]
Wu, Hao-Lin [1 ,2 ]
Nan, Xiao-Lei [1 ,2 ]
Li, Xu-Bing [1 ,2 ]
Chen, Bin [1 ,2 ]
Tung, Chen-Ho [1 ,2 ]
Wu, Li-Zhu [1 ,2 ]
机构
[1] Chinese Acad Sci, Tech Inst Phys & Chem, Key Lab Photochem Convers & Optoelect Mat, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, Sch Future Technol, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
ARYL HALIDES; DIRECT SELENATION; EFFICIENT; FUNCTIONALIZATION; CATALYST; SYSTEM; ELECTROCHEMISTRY; DISELENIDES; ACID;
D O I
10.1021/acs.orglett.0c01050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct C-S bond coupling is an attractive way to construct aryl sulfur ether, a building block for a variety of biological active molecules. Herein, we disclose an effective model for regioselective thiolation of the aromatic C-H bond by thiol activation instead of arene activation. Strikingly, this method has been applied into anisole derivatives that are not available in the arene activation approach to forge a single thioether isomer with high reactivity.
引用
收藏
页码:3804 / 3809
页数:6
相关论文
共 63 条
[1]   Resting State and Elementary Steps of the Coupling of Aryl Halides with Thiols Catalyzed by Alkylbisphosphine Complexes of Palladium [J].
Alvaro, Elsa ;
Hartwig, John F. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (22) :7858-7868
[2]   Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].
Beletskaya, Irina P. ;
Ananikov, Valentine P. .
CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636
[3]   Photocatalytic Activation of Less Reactive Bonds and Their Functionalization via Hydrogen-Evolution Cross-Couplings [J].
Chen, Bin ;
Wu, Li-Zhu ;
Tung, Chen-Ho .
ACCOUNTS OF CHEMICAL RESEARCH, 2018, 51 (10) :2512-2523
[4]   Highly regioselective synthesis of aryl chalcogenides through C-H functionalization of arenes [J].
Cheng, Jun-Hao ;
Yi, Chih-Lun ;
Liu, Tsung-Jui ;
Lee, Chin-Fa .
CHEMICAL COMMUNICATIONS, 2012, 48 (67) :8440-8442
[5]   Iodine(III) Enabled Dehydrogenative Aryl C-S Coupling by insitu Generated Sulfenium Ion [J].
Choudhuri, Khokan ;
Maiti, Saikat ;
Mal, Prasenjit .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) :1092-1101
[6]   Cu(II)-Mediated Methylthiolation of Aryl C-H Bonds with DMSO [J].
Chu, Lingling ;
Yue, Xuyi ;
Qing, Feng-Ling .
ORGANIC LETTERS, 2010, 12 (07) :1644-1647
[7]   Enzymatic Carbon-Sulfur Bond Formation in Natural Product Biosynthesis [J].
Dunbar, Kyle L. ;
Scharf, Daniel H. ;
Litomska, Agnieszka ;
Hertweck, Christian .
CHEMICAL REVIEWS, 2017, 117 (08) :5521-5577
[8]   Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry [J].
Feng, Minghao ;
Tang, Bingqing ;
Liang, Steven H. ;
Jiang, Xuefeng .
CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (11) :1200-1216
[9]   A general and long-lived catalyst for the palladium-catalyzed coupling of aryl halides with thiols [J].
Fernández-Rodríguez, MA ;
Shen, QL ;
Hartwig, JF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (07) :2180-2181
[10]   Catalyst- and Supporting-Electrolyte-Free Electrosynthesis of Benzothiazoles and Thiazolopyridines in Continuous Flow [J].
Folgueiras-Amador, Ana A. ;
Qian, Xiang-Yang ;
Xu, Hai-Chao ;
Wirth, Thomas .
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (02) :487-491