Syntheses of functionalized benzocoumarins by photoredox catalysis

被引:3
作者
Lai, Qihong [1 ]
Chen, Shanyi [1 ]
Zou, Linnan [1 ]
Lin, Chengzhi [1 ]
Huang, Shuling [1 ]
Fu, Lailing [1 ]
Cai, Lina [1 ]
Cai, Shunyou [1 ,2 ]
机构
[1] Minnan Normal Univ, Sch Chem Chem Engn & Environm, Fujian Prov Key Lab Modern Analyt Sci & Separat Te, Zhangzhou 363000, Peoples R China
[2] Peking Univ, Guangdong Prov Key Lab Chem Genom, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
基金
中国国家自然科学基金;
关键词
ALIPHATIC CARBOXYLIC-ACIDS; C-H FUNCTIONALIZATION; OXYGENATION REACTIONS; OXIDATION; LACTONIZATION; ACTIVATION; ALCOHOLS; BONDS;
D O I
10.1039/d2ob02225g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct functionalization of inert C(sp(3))-H bonds is an attractive synthetic technology for the preparation of pharmaceutically significant compounds in modern synthetic organic chemistry. In this work, we report a new method for the synthesis of functionalized benzocoumarins through the strategy of activation of multiple C-H bonds on 2-aryl toluenes under visible-light-enabled photoredox conditions. This method has the advantages of high functional group compatibility, mild reaction conditions, and effectively avoiding the use of strong oxidants and precious metal catalysts. Detailed mechanistic investigations, including spectroscopic and electrochemical studies, support the reaction's mechanistic course.
引用
收藏
页码:1181 / 1186
页数:6
相关论文
共 80 条
[1]   Aerobic Copper-Catalyzed Organic Reactions [J].
Allen, Scott E. ;
Walvoord, Ryan R. ;
Padilla-Salinas, Rosaura ;
Kozlowski, Marisa C. .
CHEMICAL REVIEWS, 2013, 113 (08) :6234-6458
[2]   A STUDY OF CHEMICAL CARCINOGENESIS .109. OXIDATION OF POLYNUCLEAR AROMATIC-HYDROCARBONS WITH CERIC AMMONIUM-SULFATE - PREPARATION OF QUINONES AND LACTONES [J].
BALANIKAS, G ;
HUSSAIN, N ;
AMIN, S ;
HECHT, SS .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1007-1010
[3]   Contra-thermodynamic Hydrogen Atom Abstraction in the Selective C-H Functionalization of Trialkylamine N-CH3 Groups [J].
Barham, Joshua P. ;
John, Matthew P. ;
Murphy, John A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (47) :15482-15487
[4]   Visible-Light Photocatalyzed peri-(3+2) Cycloadditions of Quinolines [J].
Bellotti, Peter ;
Rogge, Torben ;
Paulus, Fritz ;
Laskar, Ranjini ;
Rendel, Nils ;
Ma, Jiajia ;
Houk, K. N. ;
Glorius, Frank .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (34) :15662-15671
[5]   Visible-Light-Mediated Oxygenation Reactions using Molecular Oxygen [J].
Bian, Changliang ;
Singh, Atul K. ;
Niu, Linbin ;
Yi, Hong ;
Lei, Aiwen .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (04) :386-396
[6]   Visible light-mediated C-P bond formation reactions [J].
Cai, Bao-Gui ;
Xuan, Jun ;
Xiao, Wen-Jing .
SCIENCE BULLETIN, 2019, 64 (05) :337-350
[7]   Carbotrifluoromethylation of Allylic Alcohols via 1,2-Aryl Migration Promoted by Visible-Light-Induced Photoredox Catalysis [J].
Cai, Shunyou ;
Tian, Yu ;
Zhang, Jinwang ;
Liu, Zhiji ;
Lu, Maojian ;
Weng, Wen ;
Huang, Mingqiang .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (21) :4084-4088
[8]   Visible-Light-Enabled Decarboxylative Sulfonylation of Cinnamic Acids with Sulfonylhydrazides under Transition-Metal-Free Conditions [J].
Cai, Shunyou ;
Xu, Yaohui ;
Chen, Danling ;
Li, Lihuang ;
Chen, Qifa ;
Huang, Mingqiang ;
Weng, Wen .
ORGANIC LETTERS, 2016, 18 (12) :2990-2993
[9]   Visible-light-promoted syntheses of β-keto sulfones from alkynes and sulfonylhydrazides [J].
Cai, Shunyou ;
Chen, Danling ;
Xu, Yaohui ;
Weng, Wen ;
Li, Lihuang ;
Zhang, Ruijie ;
Huang, Mingqiang .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (18) :4205-4209
[10]   Photocatalysis in the Life Science Industry [J].
Candish, Lisa ;
Collins, Karl D. ;
Cook, Gemma C. ;
Douglas, James J. ;
Gomez-Suarez, Adrian ;
Jolit, Anais ;
Keess, Sebastian .
CHEMICAL REVIEWS, 2022, 122 (02) :2907-2980