Recent advances in copper-catalyzed multicomponent reactions with photoinduction

被引:1
作者
Song, Liangliang [1 ]
Cai, Lingchao [1 ]
van der Eycken, Erik, V [2 ,3 ]
Gong, Lei [4 ,5 ]
机构
[1] Nanjing Forestry Univ, Coll Chem Engn, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat Fo, Int Innovat Ctr Forest Chem & Mat, Nanjing 210037, Jiangsu, Peoples R China
[2] Univ Leuven, KU Leuven, Dept Chem, Lab Organ & Microwave Assisted Chem LOMAC, Celestijnenlaan 200F, B-3001 Leuven, Belgium
[3] Peoples Friendship Univ Russia RUDN Univ, Miklukho Maklaya St 6, Moscow 117198, Russia
[4] Xiamen Univ, Coll Chem & Chem Engn, Key Lab Chem Biol Fujian Prov, Xiamen, Fujian, Peoples R China
[5] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang, Peoples R China
基金
中国国家自然科学基金;
关键词
Copper; Photocatalysis; Multicomponent reaction; Radical; Asymmetric catalysis; TERMINAL ALKYNES; MERGING PHOTOREDOX; REGIOSELECTIVE SYNTHESIS; CYANOFLUOROALKYLATION; HETEROCYCLES; ALKYLATION; ALKENES;
D O I
10.1016/j.ccr.2024.216428
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Copper-catalyzed multicomponent reactions (MCRs) have garnered growing attention from synthetic chemists, due to their compelling attributes, such as cost-effectiveness, low toxicity, versatility in orchestrating one or twoelectron processes, and the extraordinary capacity to enhance molecular complexity in a single step. The synergistic combination of these reactions with photocatalysis paves the way for novel reaction pathways, offering opportunities for new transformations executed under gentler, more environmentally-friendly conditions. Copper's catalytic prowess is further underscored by its adept management of key intermediate stability and reactivity within photochemical frameworks, a testament to its multifaceted utility. Furthermore, the strategic introduction of suitable chiral ligands enables photoinduced copper-catalyzed asymmetric MCRs, streamlining the synthesis of a variety of new chiral compounds in an atom- and step-economical manner. This review aims to comprehensively encapsulate the recent advancements in photoinduced copper-catalyzed MCRs, including racemic and asymmetric fashions, dissecting the underlying reaction mechanisms, and charting a course for future explorations in this promising field.
引用
收藏
页数:19
相关论文
共 81 条
[1]   Trifluoromethylchlorosulfonylation of Alkenes: Evidence for an Inner-Sphere Mechanism by a Copper Phenanthroline Photoredox Catalyst [J].
Bagal, Dattatraya B. ;
Kachkovskyi, Georgiy ;
Knorn, Matthias ;
Rawner, Thomas ;
Bhanage, Bhalchandra M. ;
Reiser, Oliver .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (24) :6999-7002
[2]   Acyl Radical Chemistry via Visible-Light Photoredox Catalysis [J].
Banerjee, Arghya ;
Lei, Zhen ;
Ngai, Ming-Yu .
SYNTHESIS-STUTTGART, 2019, 51 (02) :303-333
[3]   P/N Heteroleptic Cu(I)-Photosensitizer-Catalyzed Deoxygenative Radical Alkylation of Aromatic Alkynes with Alkyl Aldehydes Using Dipropylamine as a Traceless Linker Agent [J].
Bao, Hanyang ;
Zhou, Bingwei ;
Luo, Shu-Ping ;
Xu, Zheng ;
Jin, Hongwei ;
Liu, Yunkui .
ACS CATALYSIS, 2020, 10 (14) :7563-7572
[4]   Site-selective and versatile aromatic C-H functionalization by thianthrenation [J].
Berger, Florian ;
Plutschack, Matthew B. ;
Riegger, Julian ;
Yu, Wanwan ;
Speicher, Samira ;
Ho, Matthew ;
Frank, Nils ;
Ritter, Tobias .
NATURE, 2019, 567 (7747) :223-228
[5]   Visible-Light-Induced Photoredox-Catalyzed Selective 1,4-Difluoroalkylesterification of 1-Aryl-1,3-dienes [J].
Bi, Ming-Hang ;
Cheng, Ying ;
Xiao, Wen-Jing ;
Chen, Jia-Rong .
ORGANIC LETTERS, 2022, :7589-7594
[6]   Higher-order multicomponent reactions: beyond four reactants [J].
Brauch, Sebastian ;
van Berkel, Sander S. ;
Westermann, Bernhard .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (12) :4948-4962
[7]   Photoinduced Copper-Catalyzed Late-Stage Azidoarylation of Alkenes via Arylthianthrenium Salts [J].
Cai, Yuan ;
Chatterjee, Sagnik ;
Ritter, Tobias .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (25) :13542-13548
[8]   Facile synthesis of fully substituted 1H-imidazoles from oxime esters via dual photoredox/copper catalyzed multicomponent reactions [J].
Cao, Shujun ;
Ma, Chongchong ;
Teng, Xinjie ;
Chen, Rongshun ;
Li, Yun ;
Yuan, Weidong ;
Zhu, Yingguang .
ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (24) :6817-6825
[9]   Bifunctional Copper-Based Photocatalyst for Reductive Pinacol-Type Couplings [J].
Caron, Antoine ;
Morin, Emilie ;
Collins, Shawn K. .
ACS CATALYSIS, 2019, 9 (10) :9458-9464
[10]   Photoinduced, Copper-Catalyzed Radical Cross-Coupling of Cycloketone Oxime Esters, Alkenes, and Terminal Alkynes [J].
Chen, Jun ;
He, Bin-Qing ;
Wang, Peng-Zi ;
Yu, Xiao-Ye ;
Zhao, Quan-Qing ;
Chen, Jia-Rong ;
Xiao, Wen-Jing .
ORGANIC LETTERS, 2019, 21 (11) :4359-4364