Ligand-Enabled Arylation of -C-H Bonds

被引:83
|
作者
Li, Suhua [1 ]
Zhu, Ru-Yi [1 ]
Xiao, Kai-Jiong [1 ]
Yu, Jin-Quan [1 ]
机构
[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
关键词
arylation; carboxylic acids; palladium; quinoline ligand; -C-H activation; ALPHA-AMINO-ACIDS; CATALYZED INTRAMOLECULAR AMINATION; UNACTIVATED C(SP(3))-H BONDS; LATE-STAGE DIVERSIFICATION; STEREOSELECTIVE-SYNTHESIS; C(SP(2))-H BONDS; ETHER SYNTHESIS; FUNCTIONALIZATION; ALKYLATION; SP(2);
D O I
10.1002/anie.201512020
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Pd-II-catalyzed arylation of -C(sp(3))-H bonds of aliphatic acid-derived amides was developed by using quinoline-based ligands. Various -aryl--amino acids were prepared from natural amino acids using this method. The influence of ligand structure on reactivity was also systematically investigated.
引用
收藏
页码:4317 / 4321
页数:5
相关论文
共 50 条
  • [1] Ligand-Enabled β-C-H Arylation of α-Amino Acids Using a Simple and Practical Auxiliary
    Chen, Gang
    Shigenari, Toshihiko
    Jain, Pankaj
    Zhang, Zhipeng
    Jin, Zhong
    He, Jian
    Li, Suhua
    Mapelli, Claudio
    Miller, Michael M.
    Poss, Michael A.
    Scola, Paul M.
    Yeung, Kap-Sun
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (09) : 3338 - 3351
  • [2] Ligand-Enabled β-C-H Arylation of α-Amino Acids Without Installing Exogenous Directing Groups
    Chen, Gang
    Zhuang, Zhe
    Li, Gen-Cheng
    Saint-Denis, Tyler G.
    Hsiao, Yi
    Joe, Candice L.
    Yu, Jin-Quan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (06) : 1506 - 1509
  • [3] Ruthenium-Catalyzed Ligand-Enabled Regiodivergent Difluoroallylation of Aryl C-H Bonds
    Shi, Chang-Yun
    Chen, Xiao-Qu
    Zeng, Ruoqing
    Lu, Heng
    Fan, Zhoulong
    Zhang, Ao
    ORGANIC LETTERS, 2023, 25 (21) : 3870 - 3875
  • [4] Dual Ligand-Enabled Nondirected C-H Cyanation of Arenes
    Chen, Hao
    Mondal, Arup
    Wedi, Philipp
    van Gemmeren, Manuel
    ACS CATALYSIS, 2019, 9 (03): : 1979 - 1984
  • [5] Dual Ligand-Enabled Nondirected C-H Olefination of Arenes
    Chen, Hao
    Wedi, Philipp
    Meyer, Tim
    Tavakoli, Ghazal
    van Gemmeren, Manuel
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (09) : 2497 - 2501
  • [6] Ligand-Enabled Catalytic C-H Arylation of Aliphatic Amines by a Four-Membered-Ring Cyclopalladation Pathway
    He, Chuan
    Gaunt, Matthew J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (52) : 15840 - 15844
  • [7] Thioether Ligand-Enabled Cationic Palladium(II)-Catalyzed Electrophilic C-H Arylation of α,β-Unsaturated Oxime Ethers
    Yamada, Takahiro
    Hashimoto, Yoshimitsu
    Tanaka, Kosaku, III
    Morita, Nobuyoshi
    Tamura, Osamu
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (19): : 12315 - 12328
  • [8] Synthesis of π-Expanded Coumarins by Ligand-Enabled Selective C-H Functionalization
    Ren, Peng
    He, Zhijie
    Xing, Tiantian
    Manar, Krishna K.
    Sampson, Jessica
    Jin, Jian
    Wang, Long
    Carrow, Brad P.
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (18) : 3155 - 3160
  • [9] Ligand-Enabled Meta-C-H Alkylation and Arylation Using a Modified Norbornene
    Shen, Peng-Xiang
    Wang, Xiao-Chen
    Wang, Peng
    Zhu, Ru-Yi
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (36) : 11574 - 11577
  • [10] Ligand-Enabled γ-C-H Olefination and Carbonylation: Construction of β-Quaternary Carbon Centers
    Li, Suhua
    Chen, Gang
    Feng, Chen-Guo
    Gong, Wei
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (14) : 5267 - 5270