Photocatalytic hydrogen atom transfer: the philosopher's stone for late-stage functionalization?

被引:179
作者
Capaldo, Luca [1 ]
Quadri, Lorenzo Lafayette [1 ]
Ravelli, Davide [1 ]
机构
[1] Univ Pavia, Dept Chem, PhotoGreen Lab, Viale Taramelli 12, I-27100 Pavia, Italy
关键词
C-H BONDS; LIGHT PHOTOREDOX CATALYSIS; DECATUNGSTATE ANION; C(SP(3))-H BONDS; TRANSFER HAT; ALKOXYL RADICALS; DIRECT ARYLATION; FLUORINATION; SELECTIVITY; ACTIVATION;
D O I
10.1039/d0gc01035a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An overview about the potentialities of photocatalytic Hydrogen Atom Transfer (HAT) for the Late-Stage Functionalization (LSF) of complex molecules is offered. The examined approach allows the smooth homolytic cleavage of the C-H bonds embedded in the substrate, offering a straightforward access to valuabe C-centred radical intermediates to be exploited for the desired transformations. The examples have been classified according to the species responsible for the activation of the substrate, also showcasing the opportunities in terms of selectivity offered by the different alternatives.
引用
收藏
页码:3376 / 3396
页数:21
相关论文
共 102 条
[1]  
Albini A, 2013, PHOTOCHEMICALLY-GENERATED INTERMEDIATES IN SYNTHESIS, P1, DOI 10.1002/9781118689202
[2]   Green chemistry and photochemistry were born at the same time [J].
Albini, A ;
Fagnoni, M .
GREEN CHEMISTRY, 2004, 6 (01) :1-6
[3]   Photochemically induced radical alkenylation of C(sp3)-H bonds [J].
Amaoka, Yuuki ;
Nagatomo, Masanori ;
Watanabe, Mizuki ;
Tao, Keisuke ;
Kamijo, Shin ;
Inoue, Masayuki .
CHEMICAL SCIENCE, 2014, 5 (11) :4339-4345
[4]  
[Anonymous], 2022, HDB BOND DISSOCIATIO
[5]  
Arevalo M.J., 2016, Click Reactions in Organic Synthesis, P77, DOI [DOI 10.1002/9783527694174.CH3, 10.1002/9783527694174.ch3]
[6]   Controlled Photocatalytic Hydrocarbon Oxidation by Uranyl Complexes [J].
Arnold, Polly L. ;
Purkis, Jamie M. ;
Rutkauskaite, Ryte ;
Kovacs, Daniel ;
Love, Jason B. ;
Austin, Jonathan .
CHEMCATCHEM, 2019, 11 (16) :3786-3790
[7]   Activation and Deactivation Strategies Promoted by Medium Effects for Selective Aliphatic C-H Bond Functionalization [J].
Bietti, Massimo .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (51) :16618-16637
[8]   Bond dissociation energies of organic molecules [J].
Blanksby, SJ ;
Ellison, GB .
ACCOUNTS OF CHEMICAL RESEARCH, 2003, 36 (04) :255-263
[9]   Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry [J].
Bogdos, Michael K. ;
Pinard, Emmanuel ;
Murphy, John A. .
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2018, 14 :2035-2064
[10]   A Continuous-Flow Protocol for Light-Induced Benzylic Fluorinations [J].
Cantillo, David ;
de Frutos, Oscar ;
Rincon, Juan A. ;
Mateos, Carlos ;
Kappe, C. Oliver .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (17) :8486-8490