Research Progress of Visible Light Promoted C-N Bond Fracture to Construct C-C Bond

被引:6
作者
Pu Jiaxia [1 ]
Jia Xiaoying [1 ]
Han Lirong [1 ]
Li Qinghan [1 ]
机构
[1] Southwest Minzu Univ, Coll Chem & Environm, Chengdu 610041, Peoples R China
关键词
diazonium salt; ammonium salt; Katritzky salt; photocatalysis; C-N bond fracture; C-C bond formation; research progress; CROSS-COUPLING REACTION; DONOR-ACCEPTOR COMPLEX; AMMONIUM-SALTS; PHOTOREDOX CATALYSIS; ALIPHATIC-AMINES; ALKYLATION; ARYLATION; ACTIVATION; CYCLIZATION; ALLYLATION;
D O I
10.6023/cjoc202302002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In recent years, the photochemical organic transformation promoted by visible light has aroused the interest of organic chemists. Compared with traditional methods, photoredox catalysis using visible light as renewable energy has been proved to be a mild and powerful tool, which can promote the activation of organic molecules by single electron transfer (SET) process. There are a lot of amino functional groups in the structures of many natural products, and amino groups are also important structural units of some drug molecules and functional materials. Therefore, by activating the C-N bond in these substances and carrying out some coupling reactions of C-C bond formation, the structure of these compounds can be effectively modified, so as to obtain compounds with various structures and functionalization. Therefore, this study has become an important research field of organic synthesis. The research results of C-N bond breaking promoted by visible light and its application in the study of C-C bond formation reaction in recent years are reviewed, and representative examples and reaction mechanisms are discussed.
引用
收藏
页码:2591 / 2613
页数:23
相关论文
共 87 条
[31]   Visible light-mediated gold-catalysed carbon(sp2)-carbon(sp) cross-coupling [J].
Kim, Suhong ;
Rojas-Martin, Jaime ;
Toste, F. Dean .
CHEMICAL SCIENCE, 2016, 7 (01) :85-88
[32]   Regioselective C-3-alkylation of quinoxalin-2(1H)-ones via C-N bond cleavage of amine derived Katritzky salts enabled by continuous-flow photoredox catalysis [J].
Kishor, Gandhari ;
Ramesh, Vankudoth ;
Rao, Vadithya Ranga ;
Pabbaraja, Srihari ;
Adiyala, Praveen Reddy .
RSC ADVANCES, 2022, 12 (20) :12235-12241
[33]   Visible light-induced hydroxyalkylation of 2H-benzothiazoles with alcohols via selectfluor oxidation [J].
Kong, Yaolei ;
Xu, Wenxiu ;
Liu, Xinghai ;
Weng, Jianquan .
CHINESE CHEMICAL LETTERS, 2020, 31 (12) :3245-3249
[34]   Photoredox Hydroxy-arylation of the Terminal Double Bond of N-Substituted 3-Methyleneisoindolin-1-ones in Visible Light [J].
Kumar, Rohit ;
Jain, Vipin Kumar ;
Jain, Nidhi .
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (18) :11939-11946
[35]   Photoinduced Deaminative Coupling of Alkylpyridium Salts with Terminal Arylalkynes [J].
Lai, Shu-Zhen ;
Yang, Yu-Ming ;
Xu, Hai ;
Tang, Zhen-Yu ;
Luo, Zhuangzhu .
JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (23) :15638-15644
[36]   Photochemical Chemoselective Alkylation of TryptophanContaining Peptides [J].
Laroche, Benjamin ;
Tang, Xinjun ;
Archer, Gaetan ;
Di Sanza, Riccardo ;
Melchiorre, Paolo .
ORGANIC LETTERS, 2021, 23 (02) :285-289
[37]   Visible Light-Promoted Radical Reactions of Diazo Compounds [J].
Li Sen ;
Zhou Lei .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (12) :3944-3958
[38]   Visible-Light-Driven External-Reductant-Free Cross-Electrophile Couplings of Tetraalkyl Ammonium Salts [J].
Liao, Li-Li ;
Cao, Guang-Mei ;
Ye, Jian-Heng ;
Sun, Guo-Quan ;
Zhou, Wen-Jun ;
Gui, Yong-Yuan ;
Yan, Si-Shun ;
Shen, Guo ;
Yu, Da-Gang .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (50) :17338-17342
[39]   Donor-Acceptor Complex Enables Cascade Radical Cyclization of N-Arylacrylamides with Katritzky Salts [J].
Lu, Yu ;
Liu, Qiang ;
Li, Bao-Lin ;
Wang, Zhi-Xiang ;
Chen, Xiang-Yu .
ORGANIC LETTERS, 2021, 23 (14) :5425-5429
[40]   Base-Promoted C-C Bond Activation Enables Radical Allylation with Homoallylic Alcohols [J].
Luebesmeyer, Maximilian ;
Mackay, Emily G. ;
Raycroft, Mark A. R. ;
Elfert, Jonas ;
Pratt, Derek A. ;
Studer, Armido .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (05) :2609-2616