Palladium-catalyzed C-H formylation of electron-rich heteroarenes through radical dichloromethylation

被引：9
|
作者：
Bao, Yan
Wang, Jian-Yong
Zhang, Ya-Xuan
Li, Yan
Wang, Xi-Sheng [1 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, 96 Jinzhai Rd, Hefei 230026, Anhui, Peoples R China
来源：
TETRAHEDRON LETTERS | 2018年 / 59卷 / 32期
基金：
美国国家科学基金会;
关键词：
Palladium-catalyzed; Formylation; Radical; Heteroarenes; BOND FUNCTIONALIZATION; NATURAL-PRODUCTS; COMPLEX; OXIDATION; INDOLES; MILD;
D O I：
10.1016/j.tetlet.2018.07.013
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel palladium-catalyzed C-H formylation of electron-rich N-, O-, and S-containing heteroarenes has been developed. The key to success is that the commercially available BrCHCl2 was used as a stoichiometric carbonyl source. Mechanistic investigations indicated that different from the known Reimer-Tiemann reaction, this net C-H formylation proceeded through an electrophilc radical-type path. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3147 / 3150
页数：4
相关论文
共 50 条
  • [21] Rhodium-Catalyzed Atroposelective Oxidative C-H/C-H Cross-Coupling Reaction of 1-Aryl Isoquinoline Derivatives with Electron-Rich Heteroarenes
    Wang, Qiang
    Zhang, Wen-Wen
    Song, Hao
    Wang, Jian
    Zheng, Chao
    Gu, Qing
    You, Shu-Li
    Journal of the American Chemical Society, 2020, 142 (37): : 15678 - 15685
  • [22] Rhodium-Catalyzed Atroposelective Oxidative C-H/C-H Cross-Coupling Reaction of 1-Aryl Isoquinoline Derivatives with Electron-Rich Heteroarenes
    Wang, Qiang
    Zhang, Wen-Wen
    Song, Hao
    Wang, Jian
    Zheng, Chao
    Gu, Qing
    You, Shu-Li
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (37) : 15678 - 15685
  • [23] Palladium-Catalyzed C-H Perfluoroalkylation of Arenes
    Loy, Rebecca N.
    Sanford, Melanie S.
    ORGANIC LETTERS, 2011, 13 (10) : 2548 - 2551
  • [24] Palladium-catalyzed amination oxidation of electron-rich olefins in green media
    Zheng, Yongpeng
    Wu, Yaodan
    Li, Jianxiao
    Wu, Wanqing
    Yang, Shaorong
    Qi, Chaorong
    Jiang, Huanfeng
    GREEN CHEMISTRY, 2025, 27 (04) : 1018 - 1022
  • [25] Palladium-Catalyzed C-H Acetoxylation Reations
    Chen, Tianbao
    Zhang, Ming
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (04) : 813 - 826
  • [26] Palladium-Catalyzed Allylic C-H Fluorination
    Braun, Marie-Gabrielle
    Doyle, Abigail G.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) : 12990 - 12993
  • [27] Palladium-Catalyzed Enantioselective Allylic Alkylations through C-H Activation
    Trost, Barry M.
    Thaisrivongs, David A.
    Donckele, Etienne J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (05) : 1523 - 1526
  • [28] Palladium(II)-Catalyzed Oxidative C-H/C-H Cross-Coupling of Heteroarenes
    Xi, Peihua
    Yang, Fan
    Qin, Song
    Zhao, Dongbing
    Lan, Jingbo
    Gao, Ge
    Hu, Changwei
    You, Jingsong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (06) : 1822 - +
  • [29] Direct C-H Phosphonylation of Electron-Rich Arenes and Heteroarenes by Visible-Light Photoredox Catalysis
    Shaikh, Rizwan S.
    Ghosh, Indrajit
    Koenig, Burkhard
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (50) : 12120 - 12124
  • [30] Palladium-Catalyzed Denitrative α-Arylation of Heteroarenes with Nitroarenes via C-H and C-NO2 Bond Activations
    Yao, Jiaxin
    Xiao, Yuxuan
    Li, Haiyan
    Yang, Xun
    Du, Jiahui
    Yin, Ying
    Feng, Lin
    Duan, Wengui
    Yu, Lin
    ORGANIC LETTERS, 2024, 26 (35) : 7307 - 7312
12345