Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis

被引:569
|
作者
Capaldo, Luca [1 ]
Ravelli, Davide [1 ]
机构
[1] Univ Pavia, Dept Chem, PhotoGreen Lab, Viale Taramelli 12, I-27100 Pavia, Italy
关键词
Photocatalysis; Hydrogen transfer; Radical reactions; C-H activation; Visible light; Photochemistry; C-H BONDS; VISIBLE-LIGHT PHOTOCATALYSIS; PHOTOREDOX CATALYSIS; C(SP(3))-H BONDS; COUPLED ELECTRON; DIRECT ARYLATION; FUNCTIONALIZATION; FLUORINATION; ABSTRACTION; ALKYLATION;
D O I
10.1002/ejoc.201601485
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The adoption of hydrogen atom transfer (HAT) in a photocatalytic approach, in which an excited catalyst is responsible for substrate activation, offers unique opportunities in organic synthesis, enabling the straightforward activation of R-H (R = C, Si, S) bonds in desired reagents. Either a direct strategy, based on the intrinsic reactivity of a limited number of photocatalysts in the excited state, or an indirect one, in which a photocatalytic cycle is used for the generation of a thermal hydrogen abstractor, can be exploited. This microreview summarizes the most recent advances (mainly from the last two years) in this rapidly developing area of research, collecting the selected examples according to the nature of the species promoting the HAT process. From the synthetic point of view, this area has led to the development of a plethora of strategies for C-C, C-Si, C-N, C-S, and C-halogen (particularly, fluorine) bond formation, as well as for oxidation reactions.
引用
收藏
页码:2056 / 2071
页数:16
相关论文
共 50 条
  • [1] Direct Photocatalyzed Hydrogen Atom Transfer (HAT) for Aliphatic C-H Bonds Elaboration
    Capaldo, Luca
    Ravelli, Davide
    Fagnoni, Maurizio
    CHEMICAL REVIEWS, 2022, 122 (02) : 1875 - 1924
  • [2] Direct C(sp2)-H activation of allenes via hydrogen-atom transfer (HAT) in organic synthesis
    Chen, Jian-Qiang
    Zhu, Gangguo
    Wu, Jie
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (07): : 2108 - 2111
  • [3] Visible light-induced bromine radical enhanced hydrogen atom transfer (HAT) reactions in organic synthesis
    Saxena, Barakha
    Patel, Roshan I.
    Sharma, Anuj
    RSC SUSTAINABILITY, 2024, 2 (08): : 2169 - 2189
  • [4] Recent advances in FeCl3-photocatalyzed organic reactions via hydrogen-atom transfer
    Yuan, Xiao-Ya
    Wang, Cong-Cong
    Yu, Bing
    CHINESE CHEMICAL LETTERS, 2024, 35 (09)
  • [5] Sequential Modifications of Metal-Organic Layer Nodes for Highly Efficient Photocatalyzed Hydrogen Atom Transfer
    Zheng, Haifeng
    Fan, Yingjie
    Blenko, Abigail L.
    Lin, Wenbin
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (18) : 9994 - 10000
  • [6] Decatungstate Photocatalyzed Acylations and Alkylations in Flow via Hydrogen Atom Transfer
    Bonassi, Filippo
    Ravelli, Davide
    Protti, Stefano
    Fagnoni, Maurizio
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (16-17) : 3687 - 3695
  • [7] Photocatalytic CH Activation by Hydrogen-Atom Transfer in Synthesis
    Protti, Stefano
    Fagnoni, Maurizio
    Ravelli, Davide
    CHEMCATCHEM, 2015, 7 (10) : 1516 - 1523
  • [8] Photoinduced intermolecular hydrogen atom transfer reactions in organic synthesis
    Cao, Hui
    Tang, Xinxin
    Tang, Haidi
    Yuan, Ye
    Wu, Jie
    CHEM CATALYSIS, 2021, 1 (03): : 523 - 598
  • [9] Photocatalyst-Free Activation of Sulfamoyl Chlorides for Regioselective Sulfamoyl-Oximation of Alkenes via Hydrogen Atom Transfer (HAT) and Halogen-Atom Transfer (XAT) Relay Strategy
    Li, Wei
    Huang, Zhihua
    Zhong, Deliang
    Li, Huaifeng
    ORGANIC LETTERS, 2024, 26 (10) : 2062 - 2067
  • [10] Controlling selectivity of hydrogen atom transfer (HAT) in photoredox catalysis
    Funes-Ardoiz, Ignacio
    Garrido-Barros, Pablo
    CHEM CATALYSIS, 2024, 4 (03):