Transition Metal Photoredox Catalysis of Radical Thiol-Ene Reactions

被引：230
|
作者：
Tyson, Elizabeth L. [1 ]
Ament, Michael S. [1 ]
Yoon, Tehshik P. [1 ]
机构：
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 05期
基金：
美国国家科学基金会; 美国国家卫生研究院;
关键词：
VISIBLE-LIGHT PHOTOCATALYSIS; C-H FUNCTIONALIZATION; ELECTRON-TRANSFER; 2+2 CYCLOADDITIONS; CHEMISTRY; EFFICIENT; BOND; SELECTIVITY; OXIDATION; ALDEHYDES;
D O I：
10.1021/jo3020825
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We describe the anti-Markovnikov hydrothiolation of olefins using visible-light-absorbing transition metal photocatalysts. The key thiyl radical intermediates are generated upon quenching of photoexcited Ru*(bpz)(3)(2) with a variety of thiols. The adducts of a wide variety of olefins and thiols are formed in excellent yield (73-99%).
引用
收藏
页码：2046 / 2050
页数：5
相关论文
共 50 条
  • [21] Applications of thiol-ene reactions in adhesives, sealants and coatings
    Woods, John
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [22] Applications of intramolecular thiol-ene reactions for the synthesis of thiosugars
    Scanlan, Eoin
    Malone, Aoife
    Corce, Vincent
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [23] Synthetic Applications of Intramolecular Thiol-Ene "Click" Reactions
    Scanlan, Eoin M.
    Corce, Vincent
    Malone, Aoife
    MOLECULES, 2014, 19 (11) : 19137 - 19151
  • [24] Novel Thiol-Ene Hybrid Coating for Metal Protection
    Taghaviksih, Mona
    Subianto, Surya
    Dutta, Naba Kumar
    Choudhury, Namita Roy
    COATINGS, 2016, 6 (02):
  • [25] Photoinitiated heterogeneous radical-mediated thiol-ene polymerizations
    Shipp, Devon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [26] Application of Thiol-yne/Thiol-ene Reactions for Peptide and Protein Macrocyclizations
    Wang, Yuanxiang
    Bruno, Benjamin J.
    Cornillie, Sean
    Nogieira, Jason M.
    Chen, Diao
    Cheatham, Thomas E., III
    Lim, Carol S.
    Chou, Danny Hung-Chieh
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (29) : 7087 - 7092
  • [27] Polynuclear heteroleptic ruthenium(II) photoredox catalysts: Evaluation in blue-light-mediated, regioselective thiol-ene reactions
    Motimani, Nozuko M.
    Ngubane, Siyabonga
    Smith, Gregory S.
    POLYHEDRON, 2022, 212
  • [28] Theoretical investigation of thiol-ene click reactions: A DFT perspective
    Findik, Volkan
    Degirmenci, Isa
    Catak, Saron
    Aviyente, Viktorya
    EUROPEAN POLYMER JOURNAL, 2019, 110 : 211 - 220
  • [29] Application of Thiol-Ene "Click" Reactions in the Preparation of Monolithic Columns
    Xiong Xiyue
    Peng Zeqiang
    Shu Yan
    He Haiqin
    Chen Yingzhuang
    Chen Bo
    PROGRESS IN CHEMISTRY, 2014, 26 (01) : 152 - 157
  • [30] Accelerated Growth of Dendrimers via Thiol-Ene and Esterification Reactions
    Montanez, Maria I.
    Campos, Luis M.
    Antoni, Per
    Hed, Yvonne
    Walter, Marie V.
    Krull, Brandon T.
    Khan, Anzar
    Hult, Anders
    Hawker, Craig J.
    Malkoch, Michael
    MACROMOLECULES, 2010, 43 (14) : 6004 - 6013
12345