Visible-Light-Mediated Cross-Couplings and C-H Activation via Dual Photoredox/Transition-Metal Catalysis in Continuous-Flow Processes

被引:10
作者
Kim, Soo Dong [1 ]
Lee, Jonghyun [1 ]
Kim, Nam-Jung [1 ]
Park, Boyoung Y. [1 ]
机构
[1] Kyung Hee Univ, Coll Pharm, Seoul 02447, South Korea
基金
新加坡国家研究基金会;
关键词
photochemical transformations; cross-coupling; C-H activation; continuous-flow processes; SINGLE-ELECTRON TRANSMETALATION; PHOTOREDOX CATALYSIS; PALLADIUM CATALYSIS; NICKEL CATALYSIS; ARYL BROMIDES; GENERATION; SILICATES; ACYLATION; BATCH; FUNCTIONALIZATION;
D O I
10.1002/ajoc.201900354
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we review dual photoredox/transition-metal catalysis for C-C/C-N cross-couplings and C-H activation in continuous-flow processes. Compared to conventional transition-metal catalysis for these reactions, visible-light-mediated synergistic catalysis enables the use of relatively mild and environmentally friendly reaction conditions by decreasing the activation energy and using a renewable energy source. However, photochemical transformations in batch processing have limitations such as reactivity, reaction time, substrate scope, and scalability due to light attenuation as represented by the Beer-Lambert law. In this review article, we therefore summarize and discuss several examples of cross-couplings and C-H activation in continuous-flow processes that overcome these problems in batch processing.
引用
收藏
页码:1578 / 1587
页数:10
相关论文
共 56 条
[1]   Improving the throughput of batch photochemical reactions using flow: Dual photoredox and nickel catalysis in flow for C(sp2)-C(sp3) cross-coupling [J].
Abdiaj, Irini ;
Alcazar, Jesus .
BIOORGANIC & MEDICINAL CHEMISTRY, 2017, 25 (23) :6190-6196
[2]   Recent synthetic additions to the visible light photoredox catalysis toolbox [J].
Angnes, Ricardo A. ;
Li, Zhou ;
Correia, Carlos Roque D. ;
Hammond, Gerald B. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (35) :9152-9167
[3]  
[Anonymous], 2015, Angew. Chem, DOI [DOI 10.1002/ANGE.201409999, 10.1002/ange.201409999]
[4]  
[Anonymous], 2015, ANGEW CHEM
[5]  
Corce V., 2015, Angewandte Chemie, V127, P11576, DOI DOI 10.1021/ol5021477
[6]   Silicates as Latent Alkyl Radical Precursors: Visible-Light Photocatalytic Oxidation of Hypervalent Bis-Catecholato Silicon Compounds [J].
Corce, Vincent ;
Chamoreau, Lise-Marie ;
Derat, Etienne ;
Goddard, Jean-Philippe ;
Ollivier, Cyril ;
Fensterbank, Louis .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (39) :11414-11418
[7]   Aryl amination using ligand-free Ni(II) salts and photoredox catalysis [J].
Corcoran, Emily B. ;
Pirnot, Michael T. ;
Lin, Shishi ;
Dreher, Spencer D. ;
DiRocco, Daniel A. ;
Davies, Ian W. ;
Buchwald, Stephen L. ;
MacMillan, David W. C. .
SCIENCE, 2016, 353 (6296) :279-283
[8]   Application of the Photoredox Coupling of Trifluoroborates and Aryl Bromides to Analog Generation Using Continuous Flow [J].
DeLano, Travis J. ;
Bandarage, Upul K. ;
Palaychuk, Natalie ;
Green, Jeremy ;
Boyd, Michael J. .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (24) :12525-12531
[9]   Merging Visible Light Photoredox Catalysis with Metal Catalyzed C-H Activations: On the Role of Oxygen and Superoxide Ions as Oxidants [J].
Fabry, David C. ;
Rueping, Magnus .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) :1969-1979
[10]   C-H Functionalization of Phenols Using Combined Ruthenium and Photoredox Catalysis: In Situ Generation of the Oxidant [J].
Fabry, David C. ;
Ronge, Meria A. ;
Zoller, Jochen ;
Rueping, Magnus .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (09) :2801-2805