A General Strategy for Organocatalytic Activation of C-H Bonds via Photoredox Catalysis: Direct Arylation of Benzylic Ethers

被引：237
|
作者：
Qvortrup, Katrine [1 ]
Rankic, Danica A. [1 ]
MacMillan, David W. C. [1 ]
机构：
[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 02期
关键词：
PHOTOCHEMICALLY INDUCED REACTIONS; COUPLED ELECTRON-TRANSFER; ENOL ETHERS; ALIPHATIC-AMINES; BETA-ARYLATION; CHEMISTRY; PYRIDINEDICARBONITRILES; ALDEHYDES; ALKENES; KETONES;
D O I：
10.1021/ja411596q
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Direct C-H functionalization and arylation of benzyl ethers has been accomplished via photoredox organocatalysis. The productive merger of a thiol catalyst and a commercially available iridium photoredox catalyst in the presence of household light directly affords benzylic arylation products in good to excellent yield. The utility of this methodology is further demonstrated in direct arylation of 2,5-dihydrofuran to form a single regioisomer.
引用
收藏
页码：626 / 629
页数：4
相关论文
共 50 条
  • [1] Enantioselective benzylic C-H arylation via photoredox and nickel dual catalysis
    Cheng, Xiaokai
    Lu, Huangzhe
    Lu, Zhan
    NATURE COMMUNICATIONS, 2019, 10 (1)
  • [2] Activation of C-H Bonds via the Merger of Photoredox and Organocatalysis: A Coupling of Benzylic Ethers with Schiff Bases
    Hager, Dominik
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (49) : 16986 - 16989
  • [3] The direct arylation of allylic sp3 C-H bonds via organic and photoredox catalysis
    Cuthbertson, James D.
    MacMillan, David W. C.
    NATURE, 2015, 519 (7541) : 74 - 77
  • [4] Direct diazomethylation of aromatic C-H bonds via photoredox catalysis
    Wang, Zhaofeng
    del Hoyo, Ana
    Herraiz, Ana
    Suero, Marcos
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [5] Nickel catalysis enables convergent paired electrolysis for direct arylation of benzylic C-H bonds
    Zhang, Lei
    Hu, Xile
    CHEMICAL SCIENCE, 2020, 11 (39) : 10786 - 10791
  • [6] Enantioselective Radical Trifluoromethylation of Benzylic C-H Bonds via Cooperative Photoredox and Copper Catalysis
    Xu, Pin
    Fan, Wenzheng
    Chen, Pinhong
    Liu, Guosheng
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (30) : 13468 - 13474
  • [7] Enantioselective benzylic C–H arylation via photoredox and nickel dual catalysis
    Xiaokai Cheng
    Huangzhe Lu
    Zhan Lu
    Nature Communications, 10
  • [8] Rationalizing the Regioselectivity of Azolation of Benzylic C-H Bonds under Photoredox Catalysis
    Sanosa, Nil
    Montiel-Cervantes, Cesar
    Rubio-Munoz, Miguel
    Sampedro, Diego
    Funes-Ardoiz, Ignacio
    SYNLETT, 2024, 35 (10) : 1149 - 1152
  • [9] Site-Selective Alkoxylation of Benzylic C-H Bonds by Photoredox Catalysis
    Lee, Byung Joo
    DeGlopper, Kimberly S.
    Yoon, Tehshik P.
    Advanced Materials, 2020, 132 (01) : 203 - 208
  • [10] Site-Selective Alkoxylation of Benzylic C-H Bonds by Photoredox Catalysis
    Lee, Byung Joo
    DeGlopper, Kimberly S.
    Yoon, Tehshik P.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (01) : 197 - 202
12345