Visible Light-Driven, Persulfate-Mediated Hydrocarboxylation of Vinylsulfones

被引:2
|
作者
Palvoelgyi, Adam Mark [1 ]
Scharinger, Fabian [1 ]
Bauhoff, Thomas [1 ]
Bica-Schroeder, Katharina [1 ]
机构
[1] TU Wien, Inst Appl Synthet Chem, Getreidemarkt 9-163, A-1060 Vienna, Austria
基金
欧洲研究理事会;
关键词
Hydrocarboxylation; CO2 radical anion; Potassium persulfate; Visible light; Hydrogen atom transfer; BETA-SELECTIVE HYDROCARBOXYLATION; C-H; CATALYZED HYDROCARBOXYLATION; CO2; STYRENES; FORMATE; HYDROXYCARBONYLATION; PHOTOCATALYSIS; ACTIVATION; COMPLEXES;
D O I
10.1002/adsc.202300654
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
We report a visible light-mediated approach for the radical hydrocarboxylation of vinylsulfone derivatives. Using cheap and easily accessible sodium formate as C1-source and K2S2O8 as reagent, a set of vinylsulfone substrates could be efficiently hydrocarboxylated in aqueous medium without any additional catalyst or reagent; and the concept could be also applied for direct hydroacylations, hydroalkylations and hydrophosphorylations. The control experiments clearly indicated that the reaction proceeds via radical mechanism without the generation of electron donor-acceptor (EDA) complexes; supporting the working model of K2S2O8-initiated in situ formation of CO2 radical anion.
引用
收藏
页码:3069 / 3074
页数:6
相关论文
共 50 条
  • [1] Visible light-driven, persulfate-mediated dual C-H sulfenylation of imidazopyridines using thiocyanate salt
    Saha, Pallavi
    Kumar, Vijay
    Sharma, Deepak K.
    New Journal of Chemistry, 2024, 48 (44) : 18651 - 18655
  • [2] Construction of a visible light-driven hydrocarboxylation cycle of alkenes by the combined use of Rh(I) and photoredox catalysts
    Murata, Kei
    Numasawa, Nobutsugu
    Shimomaki, Katsuya
    Takaya, Jun
    Iwasawa, Nobuharu
    CHEMICAL COMMUNICATIONS, 2017, 53 (21) : 3098 - 3101
  • [3] Visible light-driven conjunctive olefination
    Filippini, Dario
    Silvi, Mattia
    NATURE CHEMISTRY, 2022, 14 (01) : 66 - 70
  • [4] A visible light-driven plasmonic photocatalyst
    Francesca Pincella
    Katsuhiro Isozaki
    Kazushi Miki
    Light: Science & Applications, 2014, 3 : e133 - e133
  • [5] Visible light-driven conjunctive olefination
    Dario Filippini
    Mattia Silvi
    Nature Chemistry, 2022, 14 : 66 - 70
  • [6] A visible light-driven plasmonic photocatalyst
    Pincella, Francesca
    Isozaki, Katsuhiro
    Miki, Kazushi
    LIGHT-SCIENCE & APPLICATIONS, 2014, 3 : e133 - e133
  • [7] Visible light-driven photogeneration of hydrogen sulfide
    Yi, Seung Yeon
    Moon, Yu Kyung
    Kim, Sinheui
    Kim, Sonam
    Park, Gyurim
    Kim, Jin Ju
    You, Youngmin
    CHEMICAL COMMUNICATIONS, 2017, 53 (86) : 11830 - 11833
  • [8] Light-driven CQDs/PCN catalyzes activated persulfate degradation of bisphenol A
    Guo, Rui
    Liu, Zi-Ang
    Gao, Yi-Fang
    Jiao, Yuan
    Liu, Xiao-Na
    Qian, Tian-Wei
    Zhongguo Huanjing Kexue/China Environmental Science, 2023, 43 (01): : 164 - 173
  • [9] Organoboron Compounds in Visible Light-driven Photoredox Catalysis
    Klis, Tomasz
    Kublicki, Marcin
    CURRENT ORGANIC CHEMISTRY, 2021, 25 (09) : 994 - 1027
  • [10] Publisher Correction: Visible light-driven conjunctive olefination
    Dario Filippini
    Mattia Silvi
    Nature Chemistry, 2022, 14 (1) : 110 - 110