Site-Selective C(sp3)-H Alkenylation Using Decatungstate Anion as Photocatalyst

被引：15
|
作者：
Wang, Yi-Ting [1 ]
Shih, Yi-Lun [1 ]
Wu, Yen-Ku [1 ]
Ryu, Ilhyong [1 ,2 ]
机构：
[1] Natl Yang Ming Chiao Tung Univ NYCU, Dept Appl Chem, Hsinchu 30010, Taiwan
[2] Osaka Prefecture Univ, Org Res Promot, Sakai, Osaka 5998531, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 05期
关键词：
C(sp(3))-H alkenylation; decatungstate anion; 1; 2-bis(sulfonyl)ethylene; benzenesulfonyl radical; photocatalyst; HYDROGEN-ATOM TRANSFER; PHOTOINDUCED ALKYLATION; AMINO-ACIDS; FUNCTIONALIZATION; ALKYNYLATION; VINYLATION; CYANATION; ALKENES; ALKANES;
D O I：
10.1002/adsc.202101374
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
Site-selective C(sp(3))-H alkenylation was achieved under photo-irradiation in the presence of a catalytic amount of decatungstate anion, W10O324-. In this reaction, the radical addition/beta-scission sequence is successfully combined with photocatalytic C(sp(3))-H functionalization. The reaction using weaker C-H bonds such as those in THF revealed that the benzenesulfonyl radical itself underwent HAT directly from the C-H bond, and a decatungstate anion participated in a chain-repairing step.
引用
收藏
页码：1039 / 1043
页数：5
相关论文
共 50 条
  • [31] Bromine-Radical-Mediated Site-Selective Allylation of C(sp3)-H Bonds
    Ueda, Mitsuhiro
    Maeda, Ayami
    Hamaoka, Kanako
    Sasano, Mika
    Fukuyama, Takahide
    Ryu, Ilhyong
    SYNTHESIS-STUTTGART, 2019, 51 (05): : 1171 - 1177
  • [32] Electrochemical-Oxidation-Induced Site-Selective Intramolecular C(sp3)-H Amination
    Hu, Xia
    Zhang, Guoting
    Bu, Faxiang
    Nie, Lei
    Lei, Aiwen
    ACS CATALYSIS, 2018, 8 (10): : 9370 - 9375
  • [33] A General Catalyst for Site-Selective C(sp3)-H Bond Amination of Activated Secondary over Tertiary Alkyl C(sp3)-H Bonds
    Scamp, Ryan J.
    Jirak, James G.
    Dolan, Nicholas S.
    Guzei, Ilia A.
    Schomaker, Jennifer M.
    ORGANIC LETTERS, 2016, 18 (12) : 3014 - 3017
  • [34] Site-Selective C(sp3)-H and C(sp2)-H Functionalization of Amines Using a Directing-Group-Guided Strategy
    Kapoor, Mohit
    Singh, Adhish
    Sharma, Kirti
    Hua Hsu, Ming
    ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (21) : 4513 - 4542
  • [35] Decatungstate-photocatalysed C(sp3)-H azidation
    Lu, Yen-Chu
    Kao, Shih-Chieh
    West, Julian G.
    CHEMICAL COMMUNICATIONS, 2022, 58 (31) : 4869 - 4872
  • [36] Remote Site-Selective Radical C(sp3)-H Monodeuteration of Amides using D2O
    Wang, Lin
    Xia, Yong
    Derdau, Volker
    Studer, Armido
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (34) : 18645 - 18650
  • [37] Photoredox-Catalyzed Site-Selective α-C(sp3)-H Alkylation of Primary Amine Derivatives
    Ashley, Melissa A.
    Yamauchi, Chiaki
    Chu, John C. K.
    Otsuka, Shinya
    Yorimitsu, Hideki
    Rovis, Tomislav
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (12) : 4002 - 4006
  • [38] Direct site-selective C(sp3) - H functionalization of unprotected non-activated alcohols
    Aggarwal, Varun
    Kachore, Ankit
    Bala, Ekta
    Singh, Hemant
    Malik, Saima
    Selvaraj, Manickam
    Assiri, Mohammed A.
    Verma, Praveen Kumar
    Sharma, Upendra
    RUSSIAN CHEMICAL REVIEWS, 2024, 93 (06)
  • [39] A Site-Selective C(sp3)-H Chlorination Boosted by an Imidazolium-Functionalized Cage in Water
    Wang, Chengyi
    Tan, Chunxia
    Zhu, Yuanli
    Liu, Guohua
    Huang, Yongliang
    Liu, Rui
    ACS CATALYSIS, 2023, 13 (21) : 13896 - 13901
  • [40] Photocatalyzed Site-Selective C(sp3)-H Functionalization of Alkylpyridines at Non-Benzylic Positions
    Fukuyama, Takahide
    Nishikawa, Tomohiro
    Yamada, Keiichi
    Ravelli, Davide
    Fagnoni, Maurizio
    Ryu, Ilhyong
    ORGANIC LETTERS, 2017, 19 (23) : 6436 - 6439
12345