Visible-light-induced thiol-mediated transfer hydrogenation/deuteration of activated alkenes, imines and azo compounds

被引:0
|
作者
Xuan, Guo-Rong [1 ]
Huang, Rui-Yang [1 ]
Wu, Hua-Yue [1 ]
Liu, Miao-Chang [1 ]
Zhou, Yun-Bing [1 ,2 ]
机构
[1] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
[2] Key Lab Biohlth Mat & Chem Wenzhou, Wenzhou 325035, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2024年 / 11卷 / 24期
基金
中国国家自然科学基金;
关键词
CATALYZED TRANSFER HYDROGENATION; SAMARIUM DIIODIDE; WATER; REDUCTION; OLEFINS;
D O I
10.1039/d4qo01728e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have reported photochemical transfer hydrogenation/deuteration of activated alkenes using H2O/D2O as the H/D-source under metal-free conditions. Importantly, this protocol showed excellent chemoselectivity towards activated C 00000000 00000000 00000000 00000000 11111111 00000000 11111111 00000000 00000000 00000000 C double bonds, and good tolerance towards unactivated CC and CO bonds. Both triethylamine and thiol function as the reducing agent. Mechanistic studies implied that the photochemical olefin hydrogenation proceeds via thio-Michael addition/reductive desulfurization. Furthermore, this transformation was suitable for other unsaturated compounds containing CN and NN bonds. We have developed photochemical selective transfer hydrogenation/deuteration using H2O/D2O as the H/D-source under metal-free conditions.
引用
收藏
页码:7162 / 7167
页数:6
相关论文
共 17 条
  • [1] Visible-Light-Induced Cascade Arylazidation of Activated Alkenes with Trimethylsilyl Azide
    Wu, Xinzhuang
    Zhang, Xinyi
    Ji, Xiaochen
    Deng, Guo-Jun
    Huang, Huawen
    ORGANIC LETTERS, 2023, 25 (27) : 5162 - 5167
  • [2] Thiol-Mediated α-Amino Radical Formation via Visible-Light-Activated Ion-Pair Charge-Transfer Complexes
    Kohara, Keishi
    Trowbridge, Aaron
    Smith, Milo A.
    Gaunt, Matthew J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (46) : 19268 - 19274
  • [3] Visible-light-induced synthesis of bibenzofuranones via a cerium-mediated energy transfer process
    Lv, Jiaoyue
    Lang, Yatao
    Li, Chao-Jun
    Zeng, Huiying
    CHEMICAL COMMUNICATIONS, 2025, 61 (20) : 4054 - 4057
  • [4] Visible-Light-Induced Cascade Azidation/Cyclization of Activated Alkenes to Synthesize Azidated Indolo[2,1-a]isoquinolines
    Tang Yucai
    He Yupeng
    Yang Biyu
    Duan Jinglin
    Du Changyuan
    Jiang Jie
    Li Jiali
    Pan Ruohan
    Chen Yu
    Liu Xuewen
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (07) : 2286 - 2295
  • [5] Visible-Light-Induced Energy-Transfer-Mediated Hydrofunctionalization and Difunctionalization of Unsaturated Compounds via Sigma-Bond Homolysis of Energy-Transfer Acceptors
    Sun, Qiao
    Wang, Shao-Peng
    Xu, Yuan
    Yin, Aihua
    Yang, Liu
    Zhu, Jingheng
    Zheng, Chun-Ling
    Wang, Guowei
    Fang, Zheng
    Sui, Shanhong
    Wang, Daixi
    Dong, Yan
    Zhang, Dongshun
    Wang, Chang-Sheng
    Guo, Kai
    ACS CATALYSIS, 2025, 15 (03): : 1854 - 1941
  • [6] A New Photolabile Protecting Group for Release of Carboxylic Acids by Visible-Light-Induced Direct and Mediated Electron Transfer
    Borak, J. Brian
    Falvey, Daniel E.
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (10): : 3894 - 3899
  • [7] VISIBLE-LIGHT-INDUCED PHOTOCATALYSIS OF POLY(PYRIDINE-2,5-DIYL) - PHOTOREDUCTION OF WATER, CARBONYL-COMPOUNDS AND ALKENES WITH TRIETHYLAMINE
    MATSUOKA, S
    KOHZUKI, T
    KUWANA, Y
    NAKAMURA, A
    YANAGIDA, S
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04): : 679 - 685
  • [8] Visible-Light-Induced Three-Component 1,2-Alkylpyridylation of Alkenes via a Halogen-Atom Transfer Process
    Yu, Weijie
    Wang, Hongyu
    Zhao, Kuang
    Li, Wendong
    Wang, Tao
    Fu, Junkai
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (03): : 1703 - 1708
  • [9] Metal-Free Visible-Light-Induced Atom-Transfer Radical Addition Reaction of Alkenes/Alkynes with ICH2CN
    Pan, Chunxiang
    Meng, Yunyan
    Deng, Yao
    Zhou, Bingjie
    Chen, Jingchao
    He, Zhenxiu
    Sun, Weiqing
    Khan, Ruhima
    Fan, Baomin
    CHINESE JOURNAL OF CHEMISTRY, 2022, 40 (17) : 2040 - 2046
  • [10] Very efficient visible-light-induced uphill electron transfer at a self-assembled monolayer with a porphyrin-ferrocene-thiol linked molecule
    Uosaki, K
    Kondo, T
    Zhang, XQ
    Yanagida, M
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (35) : 8367 - 8368