Ligand-Promoted C(sp3)-H Olefination en Route to Multi-functionalized Pyrazoles

被引：26
|
作者：
Yang, Weibo [1 ]
Ye, Shengqing [1 ]
Schmidt, Yvonne [2 ]
Stamos, Dean [2 ]
Yu, Jin-Quan [1 ]
机构：
[1] Scripps Res Inst TSRI, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
[2] Vertex Pharmaceut, Med Chem, 11010 Torreyana Rd, San Diego, CA 92121 USA
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2016年 / 22卷 / 21期
关键词：
amino acid ligands; C-H activation; olefination; organic chemistry; pyrazole; C-H OLEFINATION; ALPHA-AMINO-ACIDS; BIOLOGICAL EVALUATION; SECONDARY; ARYLATION; BONDS; ACTIVATION; REAGENTS; DERIVATIVES; ALKYLATION;
D O I：
10.1002/chem.201600704
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A Pd-catalyzed/N-heterocycle-directed C(sp(3))-H olefination has been developed. The monoprotected amino acid ligand (MPAA) is found to significantly promote Pd-catalyzed C(sp(3))-H olefination for the first time. Cu(OAc)(2) instead of Ag+ salts are used as the terminal oxidant. This reaction provides a useful method for the synthesis of alkylated pyrazoles.
引用
收藏
页码：7059 / 7062
页数：4
相关论文
共 50 条
  • [1] Ligand-Enabled γ-C(sp3)-H Olefination of Amines: En Route to Pyrrolidines
    Jiang, Heng
    He, Jian
    Liu, Tao
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (06) : 2055 - 2059
  • [2] Ligand-Promoted Alkylation of C(sp3)-H and C(sp2)-H Bonds
    Zhu, Ru-Yi
    He, Jian
    Wang, Xiao-Chen
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (38) : 13194 - 13197
  • [3] Ligand-Promoted Remote γ-C(sp3)-H Chlorination and Bromination of Alcohols
    Tu, Yang-Yang
    Luo, Jun
    Jiang, Chao
    JOURNAL OF ORGANIC CHEMISTRY, 2025,
  • [4] Ligand-Promoted Borylation of C(sp3)-H Bonds with Palladium(II) Catalysts
    He, Jian
    Jiang, Heng
    Takise, Ryosuke
    Zhu, Ru-Yi
    Chen, Gang
    Dai, Hui-Xiong
    Dhar, T. G. Murali
    Shi, Jun
    Zhang, Hao
    Cheng, Peter T. W.
    Yu, Jin-Quan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (02) : 785 - 789
  • [5] Ligand-Promoted C-3 Selective C-H Olefination of Pyridines with Pd Catalysts
    Ye, Mengchun
    Gao, Guo-Lin
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (18) : 6964 - 6967
  • [6] Ligand-Promoted γ-C(sp3)-H Arylation and Unsymmetrical Diarylation to Access Unnatural Amino Acid Derivatives
    Das, Suvankar
    Bairy, Gurupada
    Jana, Ranjan
    ORGANIC LETTERS, 2018, 20 (09) : 2667 - 2671
  • [7] Ligand-Enabled γ-C(sp3)-H Olefination of Free Carboxylic Acids
    Ghosh, Kiron Kumar
    Uttry, Alexander
    Mondal, Arup
    Ghiringhelli, Francesca
    Wedi, Philipp
    van Gemmeren, Manuel
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (31) : 12848 - 12852
  • [8] Palladium-catalyzed ligand-promoted site-selective cyanomethylation of unactivated C(sp3)-H bonds with acetonitrile
    Liu, Yongbing
    Yang, Ke
    Ge, Haibo
    CHEMICAL SCIENCE, 2016, 7 (04) : 2804 - 2808
  • [9] Ligand-Enabled β-C(sp3)-H Olefination of Free Carboxylic Acids
    Zhuang, Zhe
    Yu, Chang-Bin
    Chen, Gang
    Wu, Qing-Feng
    Hsiao, Yi
    Joe, Candice L.
    Qiao, Jennifer X.
    Poss, Michael A.
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (32) : 10363 - 10367
  • [10] Ligand-Promoted Pd(II)-Catalyzed Functionalization of Unactivated C(sp3)-H Bond: Regio- and Stereoselective Synthesis of Arylated Rimantadine Derivatives
    Fan, Zhoulong
    Shu, Shiqi
    Ni, Jiabin
    Yao, Qizheng
    Zhang, Ao
    ACS CATALYSIS, 2016, 6 (02): : 769 - 774
12345