Copper-Catalyzed Chloro-Arylsulfonylation of Styrene Derivatives via the Insertion of Sulfur Dioxide

被引:19
|
作者
Li, Yue [1 ,2 ,3 ]
Shen, Lin [1 ,2 ,3 ]
Zhou, Mi [1 ,2 ,3 ]
Xiong, Baojian [1 ,2 ,3 ]
Zhang, Xuemei [1 ,2 ,3 ]
Lian, Zhong [1 ,2 ,3 ]
机构
[1] Sichuan Univ, Dept Dermatol, State Key Lab Biotherapy, Chengdu 610041, Peoples R China
[2] Sichuan Univ, Canc Ctr, Natl Clin Res Ctr Geriatr, West China Hosp, Chengdu 610041, Peoples R China
[3] Sichuan Univ, West China Sch Pharm, Chengdu 610041, Peoples R China
基金
中国国家自然科学基金;
关键词
AMINOSULFONYLATION; ALKENES;
D O I
10.1021/acs.orglett.1c02001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A copper-catalyzed four-component chloro-arylsulfonylation of styrene derivatives with aryldiazonium tetrafluor-oborates, lithium chloride, and ex-situ generated sulfur dioxide (from SOgen) is presented. This sulfonylation features good functional group compatibility, mild reaction conditions, excellent regioselectivity, and good yields. The robustness and potential of this method have also been successfully demonstrated by a gram-scale reaction. Based on experimental study, a radical-involved mechanism is proposed for the transformation.
引用
收藏
页码:5880 / 5884
页数:5
相关论文
共 50 条
  • [1] Copper-Catalyzed Trifluoromethylthio-arylsulfonylation of Styrene Derivatives via the Insertion of Sulfur Dioxide
    Chen, Gang
    Xu, Jie
    Xiong, Baojian
    Song, Hongzhuo
    Zhang, Xuemei
    Ma, Xuelei
    Lian, Zhong
    ORGANIC LETTERS, 2022, 24 (05) : 1207 - 1212
  • [2] A copper-catalyzed insertion of sulfur dioxide via radical coupling
    Zhang, Jun
    Yang, Min
    Liu, Jin-Biao
    He, Fu-Sheng
    Wu, Jie
    CHEMICAL COMMUNICATIONS, 2020, 56 (21) : 3225 - 3228
  • [3] Copper-Catalyzed 1,4-Trifluoromethylthio-Arylsulfonylation of 1,3-Enynes via the Insertion of Sulfur Dioxide
    Song, Hongzhuo
    Zhang, Xuemei
    Chen, Gang
    He, Xiaochun
    Lian, Zhong
    ORGANIC LETTERS, 2023, 25 (31) : 5916 - 5921
  • [4] Copper-catalyzed synthesis of sulfonamides from nitroarenes via the insertion of sulfur dioxide
    Wang, Xuefeng
    Yang, Min
    Kuang, Yunyan
    Liu, Jin-Biao
    Fan, Xiaona
    Wu, Jie
    CHEMICAL COMMUNICATIONS, 2020, 56 (23) : 3437 - 3440
  • [5] Copper-Catalyzed Multicomponent Oxysulfonylation of Alkenes with Cyclobutanone Oxime Esters and Hydroxamic Acids via the Insertion of Sulfur Dioxide
    Zhou, Nengneng
    Xu, Qiankun
    Xia, Ziqin
    Zhao, Fangli
    Wang, Lei
    Zhang, Man
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (23) : 4020 - 4025
  • [6] Copper-catalyzed carbene insertion into the sulfur-sulfur bond of benzenesulfonothioate
    Yuan, Hairui
    Nuligonda, Thirupathi
    Gao, Hongyin
    Tung, Chen-Ho
    Xu, Zhenghu
    ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (08): : 1371 - 1374
  • [7] Copper-Catalyzed Asymmetric Borylacylation of Styrene and Indene Derivatives
    Yang, Zhen
    Li, Peiyuan
    Lu, Hongjian
    Li, Guigen
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (06): : 4616 - 4624
  • [8] Copper-catalyzed ring-opening sulfonylation of cyclopropanols via the insertion of sulfur dioxide toward the synthesis of γ-keto aryl sulfones
    Shen, Lin
    Zhang, Xuemei
    Lian, Zhong
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (13) : 3239 - 3244
  • [9] Heterogeneous copper-catalyzed C-S coupling via insertion of sulfur dioxide: A novel and regioselective approach for the synthesis of sulfur-containing compounds
    Han, Junfen
    Wang, Kai
    You, Guirong
    Wang, Guodong
    Sun, Jian
    Duan, Guiyun
    Xia, Chengcai
    CATALYSIS COMMUNICATIONS, 2019, 128
  • [10] LIQUID SULFUR DIOXIDE CATALYZED POLYMERIZATION OF STYRENE DERIVATIVES AND FORMALDEHYDE
    TOKURA, N
    MATSUDA, M
    SHIRAI, I
    SHIINA, K
    OGAWA, Y
    KONDO, Y
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1962, 35 (06) : 1043 - 1044