Selective Fluorosulfonylation of Thianthrenium Salts Enabled by Electrochemistry

被引：43
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
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 04期
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
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  • [1] Metal-free photoredox-catalysed formal C-H/C-H coupling of arenes enabled by interrupted Pummerer activation
    Aukland, Miles H.
    Siauciulis, Mindaugas
    West, Adam
    Perry, Gregory J. P.
    Procter, David J.
    [J]. NATURE CATALYSIS, 2020, 3 (02) : 163 - 169
  • [2] The growing applications of SuFEx click chemistry
    Barrow, A. S.
    Smedley, C. J.
    Zheng, Q.
    Li, S.
    Dong, J.
    Moses, J. E.
    [J]. CHEMICAL SOCIETY REVIEWS, 2019, 48 (17) : 4731 - 4758
  • [3] Site-selective and versatile aromatic C-H functionalization by thianthrenation
    Berger, Florian
    Plutschack, Matthew B.
    Riegger, Julian
    Yu, Wanwan
    Speicher, Samira
    Ho, Matthew
    Frank, Nils
    Ritter, Tobias
    [J]. NATURE, 2019, 567 (7747) : 223 - 228
  • [4] PHASE TRANSFER CATALYSIS - PREPARATION OF ALIPHATIC AND AROMATIC SULFONYL FLUORIDES
    BIANCHI, TA
    CATE, LA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (11) : 2031 - 2032
  • [5] Enabling the Use of Alkyl Thianthrenium Salts in Cross-Coupling Reactions by Copper Catalysis
    Chen, Cheng
    Wang, Minyan
    Lu, Hongjian
    Zhao, Binlin
    Shi, Zhuangzhi
    [J]. 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
    Chen, Cheng
    Wang, Zheng-Jun
    Lu, Hongjian
    Zhao, Yue
    Shi, Zhuangzhi
    [J]. NATURE COMMUNICATIONS, 2021, 12 (01)
  • [7] Recent Advances in Thianthrenation/Phenoxathiination Enabled Site-Selective Functionalization of Arenes
    Chen, Xiao-Yue
    Wu, Yichen
    Wang, Peng
    [J]. SYNTHESIS-STUTTGART, 2022, 54 (18): : 3928 - 3940
  • [8] Pd-Catalyzed Site-SelectiveBorylation of Simple Arenes via Thianthrenation
    Chen, Xiao-Yue
    Huang, Yu-Hao
    Zhou, Jian
    Wang, Peng
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2020, 38 (11) : 1269 - 1272
  • [9] Copper(I)-catalyzed sulfonylative Suzuki-Miyaura cross-coupling
    Chen, Yiding
    Willis, Michael C.
    [J]. CHEMICAL SCIENCE, 2017, 8 (04) : 3249 - 3253
  • [10] One-pot palladium-catalyzed synthesis of sulfonyl fluorides from aryl bromides
    Davies, Alyn T.
    Curto, John M.
    Bagley, Scott W.
    Willis, Michael C.
    [J]. CHEMICAL SCIENCE, 2017, 8 (02) : 1233 - 1237
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