Selective Fluorosulfonylation of Thianthrenium Salts Enabled by Electrochemistry

被引:52
作者
Kong, Xianqiang [1 ]
Chen, Yiyi [1 ]
Liu, Qianwen [1 ]
Wang, WenJie [1 ]
Zhang, Shuangquan [1 ]
Zhang, Qian [1 ]
Chen, Xiaohui [1 ]
Xu, Yuan-Qing [2 ]
Cao, Zhong-Yan [2 ]
机构
[1] Changzhou Inst Technol, Sch Chem Engn & Mat, Changzhou 213032, Peoples R China
[2] Henan Univ, Coll Chem & Chem Engn, Kaifeng 475004, Peoples R China
关键词
SUFEX CLICK CHEMISTRY; SULFONYL FLUORIDES; GREEN;
D O I
10.1021/acs.orglett.2c03956
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical electrochemically driven method for fluorosul-fonylation of both aryl and alkyl thianthrenium salts has been disclosed. The strategy does not need external redox reagents or metal catalysts. In combination with C-H thianthrenation of aromatics, this method provides a new tool for the site-selective fluorosulfonylation of drugs.
引用
收藏
页码:581 / 586
页数:6
相关论文
共 71 条
[1]   Metal-free photoredox-catalysed formal C-H/C-H coupling of arenes enabled by interrupted Pummerer activation [J].
Aukland, Miles H. ;
Siauciulis, Mindaugas ;
West, Adam ;
Perry, Gregory J. P. ;
Procter, David J. .
NATURE CATALYSIS, 2020, 3 (02) :163-169
[2]   The growing applications of SuFEx click chemistry [J].
Barrow, A. S. ;
Smedley, C. J. ;
Zheng, Q. ;
Li, S. ;
Dong, J. ;
Moses, J. E. .
CHEMICAL SOCIETY REVIEWS, 2019, 48 (17) :4731-4758
[3]   Site-selective and versatile aromatic C-H functionalization by thianthrenation [J].
Berger, Florian ;
Plutschack, Matthew B. ;
Riegger, Julian ;
Yu, Wanwan ;
Speicher, Samira ;
Ho, Matthew ;
Frank, Nils ;
Ritter, Tobias .
NATURE, 2019, 567 (7747) :223-228
[4]   PHASE TRANSFER CATALYSIS - PREPARATION OF ALIPHATIC AND AROMATIC SULFONYL FLUORIDES [J].
BIANCHI, TA ;
CATE, LA .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (11) :2031-2032
[5]   Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis [J].
Chen, Cheng ;
Wang, Minyan ;
Lu, Hongjian ;
Zhao, Binlin ;
Shi, Zhuangzhi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (40) :21756-21760
[6]   Generation of non-stabilized alkyl radicals from thianthrenium salts for C-B and C-C bond formation [J].
Chen, Cheng ;
Wang, Zheng-Jun ;
Lu, Hongjian ;
Zhao, Yue ;
Shi, Zhuangzhi .
NATURE COMMUNICATIONS, 2021, 12 (01)
[7]   Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes [J].
Chen, Xiao-Yue ;
Wu, Yichen ;
Wang, Peng .
SYNTHESIS-STUTTGART, 2022, 54 (18) :3928-3940
[8]   Pd-Catalyzed Site-SelectiveBorylation of Simple Arenes via Thianthrenation [J].
Chen, Xiao-Yue ;
Huang, Yu-Hao ;
Zhou, Jian ;
Wang, Peng .
CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (11) :1269-1272
[9]   Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling [J].
Chen, Yiding ;
Willis, Michael C. .
CHEMICAL SCIENCE, 2017, 8 (04) :3249-3253
[10]   One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides [J].
Davies, Alyn T. ;
Curto, John M. ;
Bagley, Scott W. ;
Willis, Michael C. .
CHEMICAL SCIENCE, 2017, 8 (02) :1233-1237