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
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
  • [41] Palladium-Catalyzed Regioselective C-H Heteroarylation of Pyridotriazoles
    Rawat, Deepa
    Semwal, Rashmi
    Adimurthy, Subbarayappa
    CHEMISTRYSELECT, 2022, 7 (33):
  • [42] Palladium-Catalyzed Trifluoromethylthiolation of Aryl C-H Bonds
    Xu, Chunfa
    Shen, Qilong
    ORGANIC LETTERS, 2014, 16 (07) : 2046 - 2049
  • [43] Synthesis of Heterocyclic Compounds through Palladium-Catalyzed C-H Cyclization Processes
    Inamoto, Kiyofumi
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2013, 61 (10) : 987 - 996
  • [44] Palladium-Catalyzed Spirocyclization through C-H Activation and Regioselective Alkyne Insertion
    Yoon, Hyung
    Rolz, Martin
    Landau, Felicitas
    Lautens, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (36) : 10920 - 10923
  • [45] Palladium-catalyzed C-H activation of amide derivatives
    Daugulis, Olafs
    Shabashov, Dmitry
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233
  • [46] Palladium-Catalyzed Electrochemical C-H Alkylation of Arenes
    Yang, Qi-Liang
    Li, Chuan-Zeng
    Zhang, Liang-Wei
    Li, Yu-Yan
    Tong, Xiaofeng
    Wu, Xin-Yan
    Mei, Tian-Sheng
    ORGANOMETALLICS, 2019, 38 (06) : 1208 - 1212
  • [47] Synthesis of Biindolizines through Highly Regioselective Palladium-Catalyzed C-H Functionalization
    Xia, Ji-Bao
    Wang, Xue-Qiang
    You, Shu-Li
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01): : 456 - 458
  • [48] Palladium-Catalyzed Direct C-H Arylation of Dicyanobenzenes
    Ihanainen, Netta E.
    Kumpulainen, Esa T. T.
    Koskinen, Ari M. P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (15) : 3226 - 3229
  • [49] Palladium-Catalyzed Transformations of Alkyl C-H Bonds
    He, Jian
    Wasa, Masayuki
    Chan, Kelvin S. L.
    Shao, Ojan
    Yu, Jin-Quan
    CHEMICAL REVIEWS, 2017, 117 (13) : 8754 - 8786
  • [50] Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines
    Kim, Byeong-Seon
    Jimenez, Jacqueline
    Gao, Feng
    Wash, Patrick J.
    ORGANIC LETTERS, 2015, 17 (23) : 5788 - 5791