Spirocyclizative Remote Arylcarboxylation of Nonactivated Arenes with CO2 via Visible-Light-Induced Reductive Dearomatization

被引:40
作者
Gao, Yuzhen [1 ]
Wang, Hao [1 ]
Chi, Zhuomin [1 ,2 ]
Yang, Lei [1 ]
Zhou, Chunlin [1 ]
Li, Gang [1 ,3 ]
机构
[1] Chinese Acad Sci, Univ Chinese Acad Sci, Fujian Inst Res Struct Matter,Ctr Excellence Mol, Key Lab Coal Ethylene Glycol & Its Related Techno, Fuzhou 350002, Fujian, Peoples R China
[2] Fujian Normal Univ, Coll Chem & Mat Sci, Fuzhou 350777, Fujian, Peoples R China
[3] Shanghai Jiao Tong Univ, Frontiers Sci Ctr Transformat Mol, Shanghai 200240, Peoples R China
来源
CCS CHEMISTRY | 2022年 / 4卷 / 05期
关键词
carbon dioxide utilization; nonactivated arene; dearomatization; photocatalysis; spirocyclization; C-H CARBOXYLATION; CATALYTIC ASYMMETRIC DEAROMATIZATION; CARBON-DIOXIDE; STYRENES; ALKENES; DIFUNCTIONALIZATION; TRANSFORMATIONS; DERIVATIVES; CYCLIZATION; STRATEGIES;
D O I
10.31635/ccschem.021.202100995
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Visible-light-induced reductive dearomatization of nonactivated arenes is a very challenging transformation and remains in its infancy. Herein, we report a novel strategy to achieve a visible-light-induced spirocyclizative remote arylcarboxylation of nonactivated arenes including naphthalenyl- and phenyl-bearing aromatics with CO2 under mild conditions through a radical-polar crossover cascade (RPCC). This reductive dearomatization protocol rapidly delivers a broad range of spirocyclic and valuable carboxylic acid derivatives from readily accessible aromatic precursors with generally good regioselectivity and chemoselectivity. [GRAPHICS] .
引用
收藏
页码:1565 / 1576
页数:12
相关论文
共 101 条
[11]   Visible light-driven organic photochemical synthesis in China [J].
Chen, Yiyun ;
Lu, Liang-Qiu ;
Yu, Da-Gang ;
Zhu, Cheng-Jian ;
Xiao, Wen-Jing .
SCIENCE CHINA-CHEMISTRY, 2019, 62 (01) :24-57
[12]   Intermolecular Dearomatization of Naphthalene Derivatives by Photoredox-Catalyzed 1,2-Hydroalkylation [J].
Cheng, Yuan-Zheng ;
Huang, Xu-Lun ;
Zhuang, Wei-Hui ;
Zhao, Qing-Ru ;
Zhang, Xiao ;
Mei, Tian-Sheng ;
You, Shu-Li .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (41) :18062-18067
[13]   Asymmetric Dearomatization of Indole Derivatives with N-Hydroxycarbamates Enabled by Photoredox Catalysis [J].
Cheng, Yuan-Zheng ;
Zhao, Qing-Ru ;
Zhang, Xiao ;
You, Shu-Li .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (50) :18069-18074
[14]   Copper-Catalyzed Synthesis of Azaspirocyclohexadienones from α-Azido-N-arylamides under an Oxygen Atmosphere [J].
Chiba, Shunsuke ;
Zhang, Line ;
Lee, Jian-Yuan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7266-+
[15]   Organocatalyzed Birch Reduction Driven by Visible Light [J].
Cole, Justin P. ;
Chen, Dian-Feng ;
Kudisch, Max ;
Pearson, Ryan M. ;
Lim, Chern-Hooi ;
Miyake, Garret M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (31) :13573-13581
[16]   1,4-Hydroboration Reactions of Electron-Poor Aromatic Rings by N-Heterocyclic Carbene Boranes [J].
Dai, Wen ;
Geib, Steven J. ;
Curran, Dennis P. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (13) :6261-6267
[17]   Strategies for the Photocatalytic Generation of Carbanion Equivalents for Reductant-Free C-C Bond Formations [J].
Donabauer, Karsten ;
Koenig, Burkhard .
ACCOUNTS OF CHEMICAL RESEARCH, 2021, 54 (01) :242-252
[18]   Visible-Light-Driven Dearomatization Reaction toward the Formation of Spiro[4.5]deca-1,6,9-trien-8-ones [J].
Dong, Wuheng ;
Yuan, Yao ;
Xie, Xiaomin ;
Zhang, Zhaoguo .
ORGANIC LETTERS, 2020, 22 (02) :528-532
[19]   Light-Mediated Carboxylation Using Carbon Dioxide [J].
Fan, Zhengning ;
Zhang, Zeyu ;
Xi, Chanjuan .
CHEMSUSCHEM, 2020, 13 (23) :6201-6218
[20]   Hydroarylation of Arenes via Reductive Radical-Polar Crossover [J].
Flynn, Autumn R. ;
McDaniel, Kelly A. ;
Hughes, Meredith E. ;
Vogt, David B. ;
Jui, Nathan T. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (20) :9163-9168