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
  • [1] Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides
    Alandini, Nurtalya
    Buzzetti, Luca
    Favi, Gianfranco
    Schulte, Tim
    Candish, Lisa
    Collins, Karl D.
    Melchiorre, Paolo
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (13) : 5248 - 5253
  • [2] Bai L., CCS CHEM, V2021, P1155, DOI [10.31635/ccschem.021, DOI 10.31635/CCSCHEM.021]
  • [3] Facile allylative dearomatization catalyzed by palladium
    Bao, M
    Nakamura, H
    Yamamoto, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (04) : 759 - 760
  • [4] Recent advances in spirocyclization of indole derivatives
    Bariwal, Jitender
    Voskressensky, Leonid G.
    Van der Eycken, Erik V.
    [J]. CHEMICAL SOCIETY REVIEWS, 2018, 47 (11) : 3831 - 3848
  • [5] Reduction by dissolving metals. Part I.
    Birch, AJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1944, : 430 - 436
  • [6] ESTIMATION OF EXCITED-STATE REDOX POTENTIALS BY ELECTRON-TRANSFER QUENCHING - APPLICATION OF ELECTRON-TRANSFER THEORY TO EXCITED-STATE REDOX PROCESSES
    BOCK, CR
    CONNOR, JA
    GUTIERREZ, AR
    MEYER, TJ
    WHITTEN, DG
    SULLIVAN, BP
    NAGLE, JK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1979, 101 (17) : 4815 - 4824
  • [7] Remote sp2 C-H Carboxylation via Catalytic 1,4-Ni Migration with CO2
    Boerjesson, Marino
    Janssen-Mueller, Daniel
    Sahoo, Basudev
    Duan, Yaya
    Wang, Xueqiang
    Martin, Ruben
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (38) : 16234 - 16239
  • [8] Photochemical and Electrochemical Carbon Dioxide Utilization with Organic Compounds
    Cao, Yu
    He, Xing
    Wang, Ning
    Li, Hong-Ru
    He, Liang-Nian
    [J]. CHINESE JOURNAL OF CHEMISTRY, 2018, 36 (07) : 644 - 659
  • [9] Birch-Type Photoreduction of Arenes and Heteroarenes by Sensitized Electron Transfer
    Chatterjee, Anamitra
    Koenig, Burkhard
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (40) : 14289 - 14294
  • [10] Chen M., CCS CHEM, V2021, P69