Visible-Light Photoredox in Homolytic Aromatic Substitution: Direct Arylation of Arenes with Aryl Halides

被引：133
|
作者：
Cheng, Yannan [1 ]
Gu, Xiangyong [1 ]
Li, Pixu [1 ]
机构：
[1] Soochow Univ, Key Lab Organ Synth Jiangsu Prov, Coll Chem Chem Engn & Mat Sci, Suzhou 215123, Jiangsu, Peoples R China
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 11期
关键词：
C-H-ARYLATION; FUNCTIONALIZATION; HETEROARENES; BUTOXIDE;
D O I：
10.1021/ol400946k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Direct arylation of unactivated arenes or heteroarenes with aryl halides could be carried out in the presence of potassium tert-butoxide and dimethyl sulfoxide under visible-light irradiation. Ir(ppy)(3) was found to be an effective photoredox catalyst for this reaction. The reactions of aryl iodides occurred at room temperature. Elevated temperature was required for aryl bromides. Homolytic aromatic substitution was proposed to be the operative reaction pathway.
引用
收藏
页码：2664 / 2667
页数：4
相关论文
共 50 条
  • [31] Directing group assisted rhodium-catalyzed formal C-H arylation and carbonylative arylation of arenes with aryl halides in the presence of CO
    Teng, Houyun
    Shao, Xiaoyuan
    Zhang, Zheng-Feng
    Yang, Ke-Fang
    Su, Ming-Der
    Xu, Li-Wen
    Yang, Lei
    JOURNAL OF CATALYSIS, 2024, 429
  • [32] Sulfonylation of Aryl Halides by Visible Light/Copper Catalysis
    Yan, Qiuli
    Cui, Wenwen
    Song, Xiuyan
    Xu, Guiyun
    Jiang, Min
    Sun, Kai
    Lv, Jian
    Yang, Daoshan
    ORGANIC LETTERS, 2021, 23 (09) : 3663 - 3668
  • [33] Benign Perfluoroalkylation of Aniline Derivatives through Photoredox Organocatalysis under Visible-Light Irradiation
    Barata-Vallejo, Sebastian
    Yerien, Damian E.
    Postigo, Al
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (36) : 7869 - 7875
  • [34] Base-Promoted Homolytic Aromatic Substitution (BHAS) Reactions and Hydrodehalogenations Driven by Green Light and an Iron(III)-NHC Photoredox Catalyst
    de Groot, Lisa H. M.
    Garcia-Mateos, Clara
    Johnson, Catherine E.
    Hlynsson, Valtyr Freyr
    Sharma, Alpesh K.
    Lomoth, Reiner
    Warnmark, Kenneth
    CHEMISTRY-A EUROPEAN JOURNAL, 2025,
  • [35] Visible Light-mediated Direct Arylation of Arenes and Heteroarenes Using Diaryliodonium Salts in the Presence and Absence of a Photocatalyst
    Tobisu, Mamoru
    Furukawa, Takayuki
    Chatani, Naoto
    CHEMISTRY LETTERS, 2013, 42 (10) : 1203 - 1205
  • [36] A Combination of Visible-light Photoredox and Metal Catalysis for the Mannich-type Reaction of N-Aryl Glycine Esters
    Okamura, Izumi
    Park, Soyoung
    Han, Ji Hoon
    Notsu, Shunta
    Sugiyama, Hiroshi
    CHEMISTRY LETTERS, 2017, 46 (11) : 1597 - 1600
  • [37] Visible-Light Azidation and Chemical Patterning of Graphene via Photoredox Catalysis
    Li, Wan
    Li, Yunqi
    Wang, Bowen
    Xu, Ke
    JOURNAL OF PHYSICAL CHEMISTRY C, 2022, 126 (50) : 21281 - 21286
  • [38] Radical Fluoroalkylation of Isocyanides with Fluorinated Sulfones by Visible-Light Photoredox Catalysis
    Rong, Jian
    Deng, Ling
    Tan, Ping
    Ni, Chuanfa
    Gu, Yucheng
    Hu, Jinbo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (08) : 2743 - 2747
  • [39] Strategic Use of Visible-Light Photoredox Catalysis in Natural Product Synthesis
    Pitre, Spencer P.
    Overman, Larry E.
    CHEMICAL REVIEWS, 2022, 122 (02) : 1717 - 1751
  • [40] Synthesis of Tri- and Difluoromethoxylated Compounds by Visible-Light Photoredox Catalysis
    Lee, Johnny W.
    Lee, Katarzyna N.
    Ngai, Ming-Yu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (33) : 11171 - 11181
12345