Palladium-Catalyzed C-H Arylation of Amides by Triazole Assistance

被引：33
作者：
Santrac, Darko [1 ]
Cella, Stefano [1 ]
Wang, Wei [1 ]
Ackermann, Lutz [1 ]
机构：
[1] Georg August Univ, Inst Organ & Biomol Chem, Tammannstr 2, D-37077 Gottingen, Germany
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 32期
基金：
欧洲研究理事会;
关键词：
Synthetic methods; C-H activation; Amides; Palladium; Arenes; UNACTIVATED C(SP(3))-H BONDS; BENZOIC-ACID DERIVATIVES; DIRECTING GROUP; 1,2,3-TRIAZOLE AMINE; C(SP(2))-H BONDS; AROMATIC AMIDES; CLICK CHEMISTRY; ACTIVATION; ALKYLATION; SP(3);
D O I：
10.1002/ejoc.201601045
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Versatile palladium-catalyzed C-H arylations of benzamides were accomplished with the assistance of a removable triazole amine (TAM). The robustness of the palladium-catalyzed C-H functionalization protocol is reflected in its broad functional group tolerance, ample substrate scope, and ability to proceed under silver-free reaction conditions.
引用
收藏
页码：5429 / 5436
页数：8
相关论文
共 104 条
  • [71] Ruthenium-catalyzed ortho-C-H bond alkylation of aromatic amides with α,β- unsaturated ketones via bidentate-chelation assistance
    Rouquet, Guy
    Chatani, Naoto
    [J]. CHEMICAL SCIENCE, 2013, 4 (05) : 2201 - 2208
  • [72] Rousseau G., 2011, Angew. Chem, V123, P2498
  • [73] Removable Directing Groups in Organic Synthesis and Catalysis
    Rousseau, Geraldine
    Breit, Bernhard
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (11) : 2450 - 2494
  • [74] Oxidative Coupling of Aromatic Substrates with Alkynes and Alkenes under Rhodium Catalysis
    Satoh, Tetsuya
    Miura, Masahiro
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (37) : 11212 - 11222
  • [75] Segawa Y., 2015, ANGEW CHEM, V127, P68
  • [76] Synthesis of Extended p-Systems through C-H Activation
    Segawa, Yasutomo
    Maekawa, Takehisa
    Itami, Kenichiro
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (01) : 66 - 81
  • [77] Auxiliary-Assisted Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 Carbon-Hydrogen Bonds
    Shabashov, Dmitry
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) : 3965 - 3972
  • [78] Sharpless K.B., 2002, Angew. Chem., V114, P2708, DOI DOI 10.1002/1521-3757(20020715)114:14<2708::AID-ANGE2708>3.0.CO
  • [79] 2-0
  • [80] Transition-Metal-Catalyzed C-N Bond Forming Reactions Using Organic Azides as the Nitrogen Source: A Journey for the Mild and Versatile C-H Amination
    Shin, Kwangmin
    Kim, Hyunwoo
    Chang, Sukbok
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) : 1040 - 1052
234567891011