Visible light promoted sulfonylation and sulfonylcarbonylation of alkenes

被引:9
作者
Min, Wenjian [1 ]
Guo, Guozhe [1 ,2 ]
Yang, Caixia [1 ]
Huo, Congde [1 ]
机构
[1] Northwest Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Gansu, Peoples R China
[2] Longdong Univ, Coll Chem & Chem Engn, Qingyang 745000, Gansu, Peoples R China
基金
中国国家自然科学基金;
关键词
Alkenes; TosMIC; Vinyl sulfones; beta-Keto sulfones; Visible light; Radical; P-TOLUENESULFONYLMETHYL ISOCYANIDE; BETA-KETO SULFONES; AEROBIC DIFUNCTIONALIZATION; PROPARGYLIC ALCOHOLS; TERMINAL ALKYNES; TANDEM REACTION; DUAL ROLES; CYCLIZATION; DERIVATIVES;
D O I
10.1016/j.tetlet.2020.152029
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Visible light promoted sulfonylation and sulfonylcarbonylation reactions of readily available alkenes with TosMIC for the synthesis of valuable vinyl sulfones and beta-keto sulfones were described. A reasonable radical involved mechanism is proposed. (C) 2020 Elsevier Ltd. All rights reserved.
引用
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页数:5
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共 53 条
  • [1] Silver-catalyzed cascade reaction of tosylmethyl isocyanide (TosMIC) with propargylic alcohols to (E)-vinyl sulfones: dual roles of TosMIC
    Bounar, Haniya
    Liu, Zhenhua
    Zhang, Lin
    Guan, Xiaoxue
    Yang, Zonglian
    Liao, Peiqiu
    Bi, Xihe
    Li, Xingqi
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (32) : 8723 - 8728
  • [2] Metal-Mediated and Metal-Catalyzed Reactions of Isocyanides
    Boyarskiy, Vadim P.
    Bokach, Nadezhda A.
    Luzyanin, Konstantin V.
    Kukushkin, Vadim Yu
    [J]. CHEMICAL REVIEWS, 2015, 115 (07) : 2698 - 2779
  • [3] K2S2O8-Mediated Aerobic Oxysulfonylation of Olefins into β-Keto Sulfones in Aqueous Media
    Chawla, Ruchi
    Singh, Atul K.
    Yadav, Lal Dhar S.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (10) : 2032 - 2036
  • [4] Unexpected Role of p-Toluenesulfonylmethyl Isocyanide as a Sulfonylating Agent in Reactions with α-Bromocarbonyl Compounds
    Chen, Jiajia
    Guo, Wei
    Wang, Zhenrong
    Hu, Lin
    Chen, Fan
    Xia, Yuanzhi
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (13) : 5504 - 5512
  • [5] Oxidant-directed chemoselective sulfonylation and sulfonyloximation of alkenes via cleaving the C-S bond in TosMIC
    Chu, Xue-Qiang
    Ge, Danhua
    Loh, Teck-Peng
    Shen, Zhi-Liang
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (06) : 835 - 840
  • [6] Copper-catalyzed three-component cyclization of amidines, styrenes, and fluoroalkyl halides for the synthesis of modular fluoroalkylated pyrimidines
    Chu, Xue-Qiang
    Cheng, Bu-Qing
    Zhang, Yao-Wei
    Ge, Danhua
    Shen, Zhi-Liang
    Loh, Teck-Peng
    [J]. CHEMICAL COMMUNICATIONS, 2018, 54 (21) : 2615 - 2618
  • [7] SYNTHESIS OF SULFONES BY PHASE-TRANSFER ALKYLATION OF ARENESULFINATE SALTS
    CRANDALL, JK
    PRADAT, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (08) : 1327 - 1329
  • [8] Aminooxylation Horner-Wadsworth-Emmons Sequence for the Synthesis of Enantioenriched γ-Functionalized Vinyl Sulfones
    Doherty, William
    Evans, Paul
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (04) : 1416 - 1424
  • [9] [3+3]-Cycloaddition Reactions of α-Acidic Isocyanides with 1,3-Dipolar Azomethine Imines
    Du, Juan
    Xu, Xianxiu
    Li, Yifei
    Pan, Ling
    Liu, Qun
    [J]. ORGANIC LETTERS, 2014, 16 (15) : 4004 - 4007
  • [10] Development of DNA-Compatible Van Leusen Three-Component Imidazole Synthesis
    Geigle, Stefanie N.
    Petersen, Ann C.
    Satz, Alexander L.
    [J]. ORGANIC LETTERS, 2019, 21 (22) : 9001 - 9004