Copper-catalyzed oxidative trifluoromethylation of benzylic sp3 C-H bond adjacent to nitrogen in amines

被引：49
|
作者：
Mitsudera, Hiromasa [1 ,2 ,3 ]
Li, Chao-Jun [1 ,2 ]
机构：
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
[2] McGill Univ, FQRNT Ctr Green Chem & Catalysis, Montreal, PQ H3A 2K6, Canada
[3] Sumitomo Chem Co Ltd, Agr Chem Res Lab, Takarazuka, Hyogo 665, Japan
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 16期
基金：
加拿大自然科学与工程研究理事会;
关键词：
C-H functionalization; Copper-catalyzed; Fluorination; Oxidative coupling; Heterocycle; N-TERT-BUTANESULFINIMINES; NUCLEOPHILIC TRIFLUOROMETHYLATION; SELECTIVE INHIBITORS; CARBONYL-COMPOUNDS; SYNTHETIC METHODS; TRIMETHYL(TRIFLUOROMETHYL)SILANE; (TRIFLUOROMETHYL)TRIMETHYLSILANE; TRIFLUOROMETHYLTRIMETHYLSILANE; ALDIMINES; FLUORINE;
D O I：
10.1016/j.tetlet.2011.02.038
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Copper-catalyzed trifluoromethylation via oxidative sp(3) C-H activation at the alpha-position of nitrogen in tetrahydroisoguinoline derivatives using DDQ and Ruppert-Prakash reagent has been successfully achieved. The reaction of various amines gave the corresponding trifluoromethylated products in 15-90% yields under mild conditions. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1898 / 1900
页数：3
相关论文
共 50 条
  • [1] Copper-Catalyzed Late-Stage Benzylic C(sp3)-H Trifluoromethylation
    Xiao, Haiwen
    Liu, Zhonglin
    Shen, Haigen
    Zhang, Benxiang
    Zhu, Lin
    Li, Chaozhong
    CHEM, 2019, 5 (04): : 940 - 949
  • [2] Copper-catalyzed amidation of Sp3 C-H bonds adjacent to a nitrogen atom
    Zhang, Yongming
    Fu, Hua
    Jiang, Yuyang
    Zhao, Yufen
    ORGANIC LETTERS, 2007, 9 (19) : 3813 - 3816
  • [3] Copper-catalyzed remote C(sp3)-H azidation and oxidative trifluoromethylation of benzohydrazides
    Bao, Xu
    Wang, Qian
    Zhu, Jieping
    NATURE COMMUNICATIONS, 2019, 10 (1)
  • [4] Copper-catalyzed remote C(sp3)–H azidation and oxidative trifluoromethylation of benzohydrazides
    Xu Bao
    Qian Wang
    Jieping Zhu
    Nature Communications, 10
  • [5] Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids
    Basle, Olivier
    Li, Chao-Jun
    ORGANIC LETTERS, 2008, 10 (17) : 3661 - 3663
  • [6] Copper-Catalyzed Oxidative Benzylic C(sp3)-H Cyclization for the Synthesis of β-Lactams
    Nozawa-Kumada, Kanako
    Saga, Satoshi
    Matsuzawa, Yuta
    Hayashi, Masahito
    Shigeno, Masanori
    Kondo, Yoshinori
    CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (20) : 4496 - 4499
  • [7] Copper-catalyzed oxidative benzylic C(sp3)-H amination: direct synthesis of benzylic carbamates
    Liu, Shuai
    Achou, Raphael
    Boulanger, Coline
    Pawar, Govind
    Kumar, Nivesh
    Lusseau, Jonathan
    Robert, Frederic
    Landais, Yannick
    CHEMICAL COMMUNICATIONS, 2020, 56 (85) : 13013 - 13016
  • [8] Copper catalyzed benzylic sp3 C-H alkenylation
    Chen, Ting-An
    Staples, Richard J.
    Warren, Timothy H.
    CHEMICAL SCIENCE, 2024, 15 (42) : 17685 - 17690
  • [9] Copper-Catalyzed Direct Trifluoromethylthiolation of Benzylic C-H Bonds via Nondirected Oxidative C(sp3)-H Activation
    Chen, Chao
    Xu, Xiu-Hua
    Yang, Bin
    Qing, Feng-Ling
    ORGANIC LETTERS, 2014, 16 (12) : 3372 - 3375
  • [10] Copper-Catalyzed sp3 C-H Amination
    Gephart, Raymond T., III
    Warren, Timothy H.
    ORGANOMETALLICS, 2012, 31 (22) : 7728 - 7752
12345