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
  • [31] Palladium-Catalyzed Desulfitative C?H Arylation of Heteroarenes with Sodium Sulfinates
    Liu, Bo
    Guo, Qiang
    Cheng, Yangyang
    Lan, Jingbo
    You, Jingsong
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (48) : 13415 - 13419
  • [32] Palladium-Catalyzed Zinc-Amide-Mediated C-H Arylation of Fluoroarenes and Heteroarenes with Aryl Sulfides
    Otsuka, Shinya
    Yorimitsu, Hideki
    Osuka, Atsuhiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (42) : 14703 - 14707
  • [33] Synthesis of Redox-Active Phenanthrene-Fused Heteroarenes by Palladium-Catalyzed C-H Annulation
    Jang, Jin Hyeok
    Ahn, Seongmo
    Park, Soo Eun
    Kim, Soeun
    Byon, Hye Ryung
    Joo, Jung Min
    ORGANIC LETTERS, 2020, 22 (04) : 1280 - 1285
  • [34] Palladium-catalyzed enantioselective C-H functionalization via C-H palladation
    Zhan, Bei-Bei
    Jin, Liang
    Shi, Bing-Feng
    TRENDS IN CHEMISTRY, 2022, 4 (03): : 220 - 235
  • [35] Palladium-catalyzed regiocontrolled internal heteroarylation of electron-rich olefins with heteroaryl halides
    Xu, Dan
    Liu, Zhihua
    Tang, Weijun
    Xu, Lijin
    Hyder, Zeynab
    Xiao, Jianliang
    TETRAHEDRON LETTERS, 2008, 49 (42) : 6104 - 6107
  • [36] Palladium-catalyzed cyanation of hindered, electron-rich aryl triflates by zinc cyanide
    Kubota, H
    Rice, KC
    TETRAHEDRON LETTERS, 1998, 39 (19) : 2907 - 2910
  • [37] Allylsulfones through Palladium-Catalyzed Allylic C-H Sulfonylation of Terminal Alkenes
    Chen, Tingting
    Lahbi, Jassmin
    Broggini, Gianluigi
    Pradal, Alexandre
    Poli, Giovanni
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (08)
  • [38] Palladium-Catalyzed Electrooxidative Double C-H Arylation
    Lin, Zhipeng
    Oliveira, Joao C. A.
    Scheremetjew, Alexej
    Ackermann, Lutz
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 146 (01) : 228 - 239
  • [39] Palladium-Catalyzed Enantioselective Isodesmic C-H Iodination
    Xu Senmiao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (09) : 3325 - 3327
  • [40] Palladium-Catalyzed Oxidative Allylic C-H Silylation
    Larsson, Johanna M.
    Zhao, Tony S. N.
    Szabo, Kalmin J.
    ORGANIC LETTERS, 2011, 13 (07) : 1888 - 1891
12345