Palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides

被引：12
|
作者：
Fan, Tao [1 ]
Meng, Wei-Dong [1 ]
Zhang, Xingang [2 ]
机构：
[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, 2999 North Renmin Rd, Shanghai 201620, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
来源：
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 13卷
基金：
中国国家自然科学基金;
关键词：
alkenes; cross-coupling; Heck-type reaction; palladium; secondary trifluoromethylated alkyl bromides; COPPER-MEDIATED DIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; HALIDES; IODIDES; ALKENES; FLUORINATION; MOIETY;
D O I：
10.3762/bjoc.13.258
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient palladium-catalyzed Heck-type reaction of secondary trifluoromethylated alkyl bromides has been developed. The reaction proceeds under mild reaction conditions with high efficiency and excellent functional group tolerance, even towards formyl and hydroxy groups. Preliminary mechanistic studies reveal that a secondary trifluoromethylated alkyl radical is involved in the reaction.
引用
收藏
页码：2610 / 2616
页数：7
相关论文
共 50 条
  • [1] Palladium-Catalyzed Heck-Type Reactions of Alkyl Iodides
    Bloome, Kayla S.
    McMahen, Rebecca L.
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (50) : 20146 - 20148
  • [2] A General Synthesis of Fluoroalkylated Alkenes by Palladium-Catalyzed Heck-Type Reaction of Fluoroalkyl Bromides
    Feng, Zhang
    Min, Qiao-Qiao
    Zhao, Hai-Yang
    Gu, Ji-Wei
    Zhang, Xingang
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) : 1270 - 1274
  • [3] Palladium-Catalyzed Carbonylative Heck-Type Reactions of Alkyl Iodides
    Bloome, Kayla S.
    Alexanian, Erik J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) : 12823 - 12825
  • [4] Palladium-catalyzed intermolecular Heck-type reactions with alkyl iodides
    McMahon, Caitlin
    Alexanian, Erik
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [5] Palladium-Catalyzed Intermolecular Heck-Type Reaction of Epoxides
    Teng, Shenghan
    Tessensohn, Malcolm E.
    Webster, Richard D.
    Zhou, Jianrong Steve
    ACS CATALYSIS, 2018, 8 (08): : 7439 - 7444
  • [6] Palladium-Catalyzed Heck-Type Difluoroalkylation of Alkenes with Functionalized Difluoromethyl Bromides
    Zhang, Feng
    Min, Qiao-Qiao
    Zhang, Xingang
    SYNTHESIS-STUTTGART, 2015, 47 (19): : 2912 - 2923
  • [7] Palladium-Catalyzed Oxidative Heck-Type Alkylation/Aryl Migration/Desulfonylation between Alkenes with α-Carbonyl Alkyl Bromides
    Fan, Jian-Hong
    Yang, Ji
    Song, Ren-Jie
    Li, Jin-Heng
    ORGANIC LETTERS, 2015, 17 (04) : 836 - 839
  • [8] Palladium-Catalyzed Heck-Type Cross-Couplings of Unactivated Alkyl Iodides
    McMahon, Caitlin M.
    Alexanian, Erik J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (23) : 5974 - 5977
  • [9] Ruthenium-Catalyzed Heck-Type Alkenylation of Alkyl Bromides
    Maria Munoz-Molina, Jose
    Perez, Pedro J.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (12): : 8289 - 8296
  • [10] Novel palladium-catalyzed heck-type reaction for synthesis of chalcone derivatives
    Reichwald, C
    Kunick, C
    EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2006, 28 : S23 - S23
12345