Palladium-Catalyzed Pyrazole-Directed sp3 C-H Bond Arylation for the Synthesis of β-Phenethylamines

被引:60
|
作者
Gulia, Nurbey [1 ,2 ]
Daugulis, Olafs [1 ]
机构
[1] Univ Houston, Dept Chem, Houston, TX 77204 USA
[2] Univ Wroclaw, Dept Chem, 14 F Joliot Curie, PL-50383 Wroclaw, Poland
关键词
arenes; C-C coupling; C-H activation; homogeneous catalysis; palladium; ALPHA-AMINO-ACIDS; C(SP(3))-H ARYLATION; TRACE AMINES; ACTIVATION; FUNCTIONALIZATION; CYCLOPALLADATION; ALKYLATION; CARBON; POSITIONS; OXIDATION;
D O I
10.1002/anie.201611407
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We have developed a method for palladium-catalyzed, pyrazole-directed sp(3) C-H bond arylation by aryl iodides. The reaction employs a Pd(OAc)(2) catalyst at 5-10 mol% loading and silver(I) oxide as a halide-removal agent, and it proceeds in acetic acid or acetic acid/hexafluoroisopropanol solvent. Ozonolysis of the pyrazole moiety affords pharmaceutically important beta-phenethylamines.
引用
收藏
页码:3630 / 3634
页数:5
相关论文
共 50 条
  • [31] Palladium-Catalyzed γ-C(sp3)-H Arylation of Thiols by a Detachable Protecting/Directing Group
    Jin, Likun
    Wang, Jianchun
    Dong, Guangbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (38) : 12352 - 12355
  • [32] Ligand-Enabled, Palladium-Catalyzed β-C(sp3)-H Arylation of Weinreb Amides
    Park, Hojoon
    Chekshin, Nikita
    Shen, Peng-Xiang
    Yu, Jin-Quan
    ACS CATALYSIS, 2018, 8 (10): : 9292 - 9297
  • [33] Asymmetric construction of quaternary α-nitro amides by palladium-catalyzed C(sp3)-H arylation
    Kong, Wei-Xin
    Xie, Shi-Jing
    Cao, Chen-Yao-Zi
    Zhang, Chao-Wei
    Wang, Chuanyong
    Duan, Wei-Liang
    CHEMICAL COMMUNICATIONS, 2020, 56 (15) : 2292 - 2295
  • [34] Palladium-Catalyzed Site-Selective sp3 C-H Bond Thiocyanation of 2-Aminofurans
    Chen, Yongtao
    Wang, Shuaifeng
    Jiang, Qianwen
    Cheng, Cungui
    Xiao, Xiaohui
    Zhu, Gangguo
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (02): : 716 - 722
  • [35] Efficient Palladium-Catalyzed C-H Fluorination of C(sp3)-H Bonds: Synthesis of β-Fluorinated Carboxylic Acids
    Zhu, Qihua
    Ji, Dezhong
    Liang, Tingting
    Wang, Xueyan
    Xu, Yungen
    ORGANIC LETTERS, 2015, 17 (15) : 3798 - 3801
  • [36] Palladium-catalyzed remote internal C(sp3)-H bond chlorination of alkenes
    Wang, Yao-Xin
    Wang, Zhen
    Yang, Xiao-Hui
    NATURE COMMUNICATIONS, 2024, 15 (01)
  • [37] Palladium-Catalyzed Diacetoxylation of Methylenecyclopropanes via C(SP3)-C(SP3) Bond Breaking
    Jiang, Min
    Shi, Min
    ORGANOMETALLICS, 2009, 28 (19) : 5600 - 5602
  • [38] Palladium-catalyzed Direct C-H Bond Arylation of Simple Arenes with Aryltrimethylsilanes
    Funaki, Kenji
    Kawai, Hiroshi
    Sato, Tetsuo
    Oi, Shuichi
    CHEMISTRY LETTERS, 2011, 40 (09) : 1050 - 1052
  • [39] Palladium-Catalyzed Triarylation of sp3 C-H Bonds in Heteroarylmethanes: Synthesis of Triaryl(heteroaryl)methanes
    Zhang, Shuguang
    Hu, Bowen
    Zheng, Zhipeng
    Walsh, Patrick J.
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (07) : 1493 - 1498
  • [40] Scope and Limitations of Auxiliary-Assisted, Palladium-Catalyzed Arylation and Alkylation of sp2 and sp3 C-H Bonds
    Nadres, Enrico T.
    Santos, Gerson Ivan Franco
    Shabashov, Dmitry
    Daugulis, Olafs
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19): : 9689 - 9714