Recent synthetic additions to the visible light photoredox catalysis toolbox

被引:183
作者
Angnes, Ricardo A. [1 ]
Li, Zhou [2 ]
Correia, Carlos Roque D. [1 ]
Hammond, Gerald B. [2 ]
机构
[1] State Univ Campinas Unicamp, Inst Chem, BR-13083970 Campinas, SP, Brazil
[2] Univ Louisville, Dept Chem, Louisville, KY 40292 USA
基金
美国国家科学基金会; 巴西圣保罗研究基金会;
关键词
C-H FUNCTIONALIZATION; AEROBIC OXIDATIVE CYCLIZATION; ELECTRON-DEFICIENT ALKENES; TERTIARY ALIPHATIC-AMINES; TRANSFER RADICAL-ADDITION; DE-NOVO SYNTHESIS; DEHYDROGENATIVE-COUPLING REACTION; INTERMOLECULAR 3+2 ANNULATION; HYDROGEN EVOLUTION REACTION; TRANSITION-METAL CATALYSIS;
D O I
10.1039/c5ob01349f
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The boom in visible light photoredox catalysis (VLPC) research has demonstrated that this novel synthetic approach is here to stay. VLPC enables reactive radical intermediates to be catalytically generated at ambient temperature, a feat not generally allowed through traditional pyrolysis-or radical initiator-based methodologies. VLPC has vastly extended the range of substrates and reaction schemes that have been traditionally the domain of radical reactions. In this review the photophysics background of VLPC will be briefly discussed, followed by a report on recent inroads of VLPC into decarboxylative couplings and radical C-H functionalization of aromatic compounds. The bulk of the review will be dedicated to advances in synergistic catalysis involving VLPC, namely the combination of photoredox catalysis with organocatalysis, including beta-functionalization of carbonyl groups, functionalization of weak aliphatic C-H bonds, and anti-Markovnikov hydrofunctionalization of alkenes; dual catalysis with gold or with nickel, photoredox catalysis as an oxidation promoter in transition metal catalysis, and acid-catalyzed enantio-selective radical addition to pi systems.
引用
收藏
页码:9152 / 9167
页数:16
相关论文
共 361 条
[41]   Photoredox-Induced Three-Component Azido- and Aminotrifluoromethylation of Alkenes [J].
Dagousset, Guillaume ;
Carboni, Aude ;
Magnier, Emmanuel ;
Masson, Geraldine .
ORGANIC LETTERS, 2014, 16 (16) :4340-4343
[42]   Visible-light photoredox-mediated oxidation of N-methyl tertiaryamines under catalyst free conditions: Direct synthesis of methylene-bridged bis-1,3-dicarbonyl compounds [J].
Dai, Xiao-Jun ;
Xu, Xiao-Liang ;
Cheng, Dong-Ping ;
Li, Xiao-Nian .
CHINESE CHEMICAL LETTERS, 2014, 25 (04) :545-548
[43]   The Coupling of Tertiary Amines with Acrylate Derivatives via Visible-Light Photoredox Catalysis [J].
Dai, Xiaojun ;
Cheng, Dongping ;
Guan, Baochuan ;
Mao, Wenjuan ;
Xu, Xiaoliang ;
Li, Xiaonian .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (15) :7212-7219
[44]   Visible-light photocatalytic oxidation of 1,3-dicarbonyl compounds and carbon-carbon bond formation [J].
Daniel, Marion ;
Fensterbank, Louis ;
Goddard, Jean-Philippe ;
Ollivier, Cyril .
ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (05) :551-555
[45]   Visible-light-driven synthesis of 2-substituted benzothiazoles using CdS nanosphere as heterogenous recyclable catalyst [J].
Das, Sudipto ;
Samanta, Suvendu ;
Maji, Swarup Kumar ;
Samanta, Partha Kumar ;
Dutta, Amit Kumar ;
Srivastava, Divesh N. ;
Adhikary, Bibhutosh ;
Biswas, Papu .
TETRAHEDRON LETTERS, 2013, 54 (09) :1090-1096
[46]   IMIDYL RADICALS - THE CHEMISTRIES OF 1,8-NAPHTHALENEDICARBOXIMIDYL AND PHTHALIMIDYL RADICALS [J].
DAY, JC ;
GOVINDARAJ, N ;
MCBAIN, DS ;
SKELL, PS ;
TANKO, JM .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :4959-4963
[47]   Study of the Light-Induced Spin Crossover Process of the [FeII(bpy)3]2+ Complex [J].
de Graaf, Coen ;
Sousa, Carmen .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (15) :4550-4556
[48]   Tandem Cyclizations of 1,6-Enynes with Arylsulfonyl Chlorides by Using Visible-Light Photoredox Catalysis [J].
Deng, Guo-Bo ;
Wang, Zhi-Qiang ;
Xia, Jia-Dong ;
Qian, Peng-Cheng ;
Song, Ren-Jie ;
Hu, Ming ;
Gong, Lu-Bin ;
Li, Jin-Heng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) :1535-1538
[49]   Visible-light-induced photocatalytic oxytrifluoromethylation of N-allylamides for the synthesis of CF3-containing oxazolines and benzoxazines [J].
Deng, Qiao-Hui ;
Chen, Jia-Rong ;
Wei, Qiang ;
Zhao, Quan-Qing ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
CHEMICAL COMMUNICATIONS, 2015, 51 (17) :3537-3540
[50]   De Novo Synthesis of Imidazoles by Visible-Light-Induced Photocatalytic Aerobic Oxidation/[3+2] Cycloaddition/Aromatization Cascade [J].
Deng, Qiao-Hui ;
Zou, You-Quan ;
Lu, Liang-Qiu ;
Tang, Zi-Long ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
CHEMISTRY-AN ASIAN JOURNAL, 2014, 9 (09) :2432-2435