Copper-catalyzed thiolation of terminal aromatic alkynes to access alkynyl disulfides

被引:9
作者
Li, Junhao [1 ]
Li, Ming [1 ]
Duan, Xuelun [1 ]
Song, Wangze [1 ,2 ]
机构
[1] Dalian Univ Technol, Sch Chem Engn, Dept Pharmaceut Sci, State Key Lab Fine Chem, Dalian 116024, Peoples R China
[2] Zhongli Sci & Technol Grp Co Ltd, Changshu 215542, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
Alkynyl disulfides; Disulfur transfer; Thiolation; Copper-catalyzed; Steric hindrance; UNSYMMETRICAL DISULFANES; 1-ALKYNYL DISULFIDES; CYCLOADDITION; EFFICIENT; THIOLS; MILD;
D O I
10.1016/j.tetlet.2020.152256
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed thiolation of terminal aromatic alkynes by disulfur transfer to access alkynyl disulfides was developed. Different types of products were afforded due to the steric hindrance of dithiolsulfonates. Some important compounds, such as fully substituted triazoles and pyrene-gemcitabine conjugate were prepared by this new approach. (C) 2020 Elsevier Ltd. All rights reserved.
引用
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页数:4
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共 32 条
[1]   Rhodium-catalyzed disulfide exchange reaction [J].
Arisawa, M ;
Yamaguchi, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (22) :6624-6625
[2]   N-trifluoroacetyl arenesulfenamides, effective precursors for synthesis of unsymmetrical disulfides and sulfenamides [J].
Bao, M ;
Shimizu, M .
TETRAHEDRON, 2003, 59 (48) :9655-9659
[3]   An efficient and convenient method for preparation of disulfides from thiols using air as oxidant catalyzed by Co-Salophen [J].
Chai, Pin Ji ;
Li, Yong Shu ;
Tan, Cheng Xia .
CHINESE CHEMICAL LETTERS, 2011, 22 (12) :1403-1406
[4]   Iridium-Catalyzed Hydroxyl-Enabled Cycloaddition of Azides and Alkynes [J].
Chen, Renjie ;
Zeng, Linwei ;
Lai, Zhencheng ;
Cui, Sunliang .
ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (05) :989-994
[5]   Iridium-Catalyzed Intermolecular Azide-Alkyne Cycloaddition of Internal Thioalkynes under Mild Conditions [J].
Ding, Shengtao ;
Jia, Guochen ;
Sun, Jianwei .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (07) :1877-1880
[6]   Reusable cobalt-phthalocyanine in water: efficient catalytic aerobic oxidative coupling of thiols to construct S-N/S-S bonds [J].
Dou, Yingchao ;
Huang, Xin ;
Wang, Hao ;
Yang, Liting ;
Li, Heng ;
Yuan, Bingxin ;
Yang, Guanyu .
GREEN CHEMISTRY, 2017, 19 (11) :2491-2495
[7]   Glyco-SeS: Selenenylsulfide-mediated protein glycoconjugation - A new strategy in post-translational modification [J].
Gamblin, DP ;
Garnier, P ;
van Kasteren, S ;
Oldham, NJ ;
Fairbanks, AJ ;
Davis, BG .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (07) :828-833
[8]   Interaction between DNA Polymerase λ and Anticancer Nucleoside Analogs [J].
Garcia-Diaz, Miguel ;
Murray, Michael S. ;
Kunkel, Thomas A. ;
Chou, Kai-ming .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2010, 285 (22) :16874-16879
[9]   Multifaceted Roles of Disulfide Bonds. Peptides as Therapeutics [J].
Gongora-Benitez, Miriam ;
Tulla-Puche, Judit ;
Albericio, Fernando .
CHEMICAL REVIEWS, 2014, 114 (02) :901-926
[10]   Internal Activation of Peptidyl Prolyl Thioesters in Native Chemical Ligation [J].
Gui, Yue ;
Qiu, Lingqi ;
Li, Yaohao ;
Li, Hongxing ;
Dong, Suwei .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (14) :4890-4899