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
  • [31] Synthesis of Chlorinated Oligopeptides via γ- and δ-Selective Hydrogen Atom Transfer Enabled by the N-Chloropeptide Strategy
    Nanjo, Takeshi
    Matsumoto, Ayaka
    Oshita, Takuma
    Takemoto, Yoshiji
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (34) : 19067 - 19075
  • [32] The Merger of Photocatalyzed Hydrogen Atom Transfer with Transition Metal Catalysis for C-H Functionalization of Alkanes and Cycloalkanes
    Ye, Ziqi
    Lin, Yu-Mei
    Gong, Lei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (40) : 5545 - 5556
  • [33] Cascade cyclization for the synthesis of indolo[2,1-α]isoquinoline derivatives via visible-light-induced halogen-atom-transfer (XAT) and hydrogen-atom-transfer (HAT)
    Ma, Na
    Guo, Lin
    Shen, Zheng-Jia
    Qi, Dan
    Yang, Chao
    Xia, Wujiong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (08) : 1731 - 1737
  • [34] Formation of TEMPO Adducts with Hydrogen Atom Transfer: An Alternative Pathway to Versatile Hydrofunctionalizations of Olefins
    Yao, Chengbo
    Aliyu, Muinat A.
    Wan, Yanjun
    Norton, Jack R.
    CHEMISTRY-A EUROPEAN JOURNAL, 2025,
  • [35] Tetraethylammonium Tetraselenotungstate: A Versatile Selenium Transfer Reagent in Organic Synthesis
    Sureshkumar, Devarajulu
    Gopinath, Purushothaman
    Chandrasekaran, Srinivasan
    CHIMIA, 2012, 66 (12) : 921 - 929
  • [36] Synthesis of Cyclic Imides from Nitriles and Diols Using Hydrogen Transfer as a Substrate-Activating Strategy
    Kim, Jaewoon
    Hong, Soon Hyeok
    ORGANIC LETTERS, 2014, 16 (17) : 4404 - 4407
  • [37] Theoretical insight into decatungstate photocatalyzed alkylation of N-tosylimine via hydrogen atom transfer and proton-coupled electron transfer
    Meng, Lingying
    Dong, Yujiao
    Zhu, Bo
    Liang, Yujie
    Su, Zhongmin
    Guan, Wei
    DALTON TRANSACTIONS, 2022, 51 (20) : 7928 - 7935
  • [38] Cyclobutenyl Inimers as Versatile Initiators for Macromonomers Synthesis by Atom Transfer Radical Polymerization
    Pioge, Sandie
    Morandi, Gaelle
    Legoupy, Stephanie
    Montembault, Veronique
    Pascual, Sagrario
    Fontaine, Laurent
    MACROMOLECULES, 2008, 41 (24) : 9595 - 9601
  • [39] Implementing Hydrogen Atom Transfer (HAT) Catalysis for Rapid and Selective Reductive Photoredox Transformations in Continuous Flow
    Steiner, Alexander
    Williams, Jason D.
    Rincon, Juan A.
    de Frutos, Oscar
    Mateos, Carlos
    Kappe, C. Oliver
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (33) : 5807 - 5811
  • [40] 1,n-Hydrogen-Atom Transfer (HAT) Reactions in Which n ≠ 5: An Updated Inventory
    Nechab, Malek
    Mondal, Shovan
    Bertrand, Michele P.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (49) : 16034 - 16059