Visible light-induced hydrogen atom transfer trifluoromethylthiolation of aldehydes with bismuth catalyst

被引:6
|
作者
Dong, Jun [1 ]
Tang, Zhuang [1 ]
Zou, Luqian [1 ]
Zhou, Yongyun [2 ]
Chen, Jingchao [1 ,2 ]
机构
[1] Yunnan Minzu Univ, Key Lab Chem Ethn Med Resources, Yuehua St, Kunming 650500, Yunnan, Peoples R China
[2] Yunnan Minzu Univ, Yunnan Key Lab Chiral Funct Subst Res & Applicat, Yuehua St, Kunming 650504, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H TRIFLUOROMETHYLTHIOLATION; PHOTOREDOX CATALYSIS; DECATUNGSTATE; CHEMISTRY; FLUORINE; BONDS;
D O I
10.1039/d3cc05048c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
By using a combination of BiCl3 and TBACl as a ligand-to-metal charge transfer (LMCT) photocatalyst, hydrogen atom transfer trifluoromethylthiolation of aldehydes was achieved under visible light irradiation. The present method provides economical and operationally simple access to trifluoromethylthioesters using low toxicity and cost-effective bismuth catalysts under mild reaction conditions. Based on the radical trapping experiments, the direct conversion of aldehydes to acyl radicals via chlorine radicals as HAT reagents was proposed as the reaction mechanism. By using a combination of BiCl3 and TBACl as a ligand-to-metal charge transfer (LMCT) photocatalyst, hydrogen atom transfer trifluoromethylthiolation of aldehydes was achieved under visible light irradiation.
引用
收藏
页码:742 / 745
页数:4
相关论文
共 50 条
  • [21] Uranyl-Organic Framework as Hydrogen Atom Transfer Catalyst for Visible-Light-Driven Heterogeneous Hydroacylation of Azodicarboxylates
    Chen, Lei
    Tan, Ke-Xin
    Zheng, Zhi-Jian
    Lin, Xiao-Ling
    Ming, Bang-Ming
    Zhang, Zhi-Bin
    Yang, Guo-Ping
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (15)
  • [22] Free Radical Chemistry Enabled by Visible Light-Induced Electron Transfer
    Staveness, Daryl
    Bosque, Irene
    Stephenson, Corey R. J.
    ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (10) : 2295 - 2306
  • [23] Visible-Light-Induced Atom-Transfer-Radical Polymerization with a ppm-Level Iron Catalyst
    Bian, Chao
    Zhou, Yin-Ning
    Guo, Jun-Kang
    Luo, Zheng-Hong
    INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2017, 56 (17) : 4949 - 4956
  • [24] Visible light-induced metal-free atom transfer radical (co)polymerization of maleimides using commercial organocatalysts
    Liao, Daohong
    Chen, Ao
    Pang, Wenmin
    Tan, Chen
    Bashir, Muhammad Sohail
    JOURNAL OF APPLIED POLYMER SCIENCE, 2023, 140 (09)
  • [25] Visible Light-Induced Radical Addition/Annulation to Construct Phenylsulfonyl-Functionalized Dihydrobenzofurans Involving an Intramolecular 1,5-Hydrogen Atom Transfer Process
    Xie, Shentong
    Li, Yifan
    Liu, Ping
    Sun, Peipei
    ORGANIC LETTERS, 2020, 22 (22) : 8774 - 8779
  • [26] Visible light-mediated hydrogen atom transfer and proton transfer for the conversion of (2-vinylaryl)methanol derivatives to aryl aldehydes or aryl ketones
    Yan, Jun
    Yu, Ziqi
    Wei, Hao-Zhao
    Shi, Min
    Wei, Yin
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (23) : 5876 - 5885
  • [27] Light-Induced Activation of the Du Bois [RhII2(Esp)2] Catalyst for Nitrogen Atom Transfer Reactions
    Farran, Rajaa
    Ducloiset, Clemence
    Buendia, Julien
    Nhat Tam Vo
    Guillot, Regis
    Halime, Zakaria
    Dauban, Philippe
    Leibl, Winfried
    Sircoglou, Marie
    Aukauloo, Ally
    CHEMPHOTOCHEM, 2017, 1 (12): : 562 - 567
  • [28] Visible light-induced crosslinkable gelatin
    Son, Tae Il
    Sakuragi, Makoto
    Takahashi, Sawa
    Obuse, Sei
    Kang, Jeonghwa
    Fujishiro, Masako
    Matsushita, Haruhiko
    Gong, Jiansheng
    Shimizu, Shigeru
    Tajima, Yusuke
    Yoshida, Yasuhiro
    Suzuki, Kazuomi
    Yamamoto, Toshio
    Nakamura, Mariko
    Ito, Yoshihiro
    ACTA BIOMATERIALIA, 2010, 6 (10) : 4005 - 4010
  • [29] Visible Light-Induced Aromatic Difluoroalkylation
    Jung, Jaehun
    Kim, Eunjin
    You, Youngmin
    Cho, Eun Jin
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (13) : 2741 - 2748
  • [30] SENSITIZATION AND CATALYSIS OF LIGHT-INDUCED DECARBONYLATION OF ALDEHYDES
    BERMAN, JD
    SHERMAN, WV
    STANLEY, JH
    COHEN, SG
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (24) : 4010 - &