Ligand-Enabled Alkynylation of C(sp3)-H Bonds with Palladium(II) Catalysts

被引：46
|
作者：
Fu, Haiyan [1 ]
Shen, Peng-Xiang [1 ]
He, Jian [1 ]
Zhang, Fanglin [1 ]
Li, Suhua [1 ]
Wang, Peng [1 ]
Liu, Tao [1 ]
Yu, Jin-Quan [1 ]
机构：
[1] Scripps Res Inst, Dept Chem, 10550 North Torrey Pines Rd, La Jolla, CA 92037 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 07期
关键词：
alkynylation; amino acids; C-H activation; palladium; pyridine; C-H ALKYNYLATION; ALPHA-AMINO-ACIDS; ROOM-TEMPERATURE; TERMINAL ALKYNES; CHELATION-ASSISTANCE; C(SP(2))-H BONDS; DIRECTING GROUP; MILD CONDITIONS; DERIVATIVES; ACTIVATION;
D O I：
10.1002/anie.201610426
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The palladium(II)-catalyzed beta-and-alkynylation of amide C(sp(3))-H bonds is enabled by pyridine-based ligands. This alkynylation reaction is compatible with substrates containing alpha-tertiary or alpha-quaternary carbon centers. The beta-methylene C(sp(3))-H bonds of various carbocyclic rings were also successfully alkynylated.
引用
收藏
页码：1873 / 1876
页数：4
相关论文
共 50 条
  • [41] Palladium(0)/PAr3-Catalyzed Intermolecular Amination of C(sp3)H Bonds: Synthesis of -Amino Acids
    He, Jian
    Shigenari, Toshihiko
    Yu, Jin-Quan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (22) : 6545 - 6549
  • [42] Sulfonamide-Promoted Palladium(II)-Catalyzed Alkylation of Unactivated Methylene C(sp3)-H Bonds with Alkyl Iodides
    Chen, Kai
    Shi, Bing-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (44) : 11950 - 11954
  • [43] Ligand-Enabled β-C(sp3)-H Lactamization of Tosyl-Protected Aliphatic Amides Using a Practical Oxidant
    Zhuang, Zhe
    Liu, Shuang
    Cheng, Jin-Tang
    Yeung, Kap-Sun
    Qiao, Jennifer X.
    Meanwell, Nicholas A.
    Yu, Jin-Quan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (34)
  • [44] Roles of Ligand and Oxidant in Pd(II)-Catalyzed and Ligand-Enabled C(sp3)-H Lactonization in Aliphatic Carboxylic Acid: Mechanistic Studies
    Xu, Li-Ping
    Zhuang, Zhe
    Qian, Shaoqun
    Yu, Jin-Quan
    Musaev, Djamaladdin G.
    ACS CATALYSIS, 2022, 12 (09): : 4848 - 4858
  • [45] Ligand Enabled Pd(II)-Catalyzed γ-C(sp3)-H Lactamization of Native Amides
    Liu, Shuang
    Zhuang, Zhe
    Qiao, Jennifer X.
    Yeung, Kap-Sun
    Su, Shun
    Cherney, Emily C.
    Ruan, Zheming
    Ewing, William R.
    Poss, Michael A.
    Yu, Jin-Quan
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2021, 143 (51) : 21657 - 21666
  • [46] Palladium-Catalyzed Annulations via Sequential C-H Activations of C(sp2)-H/C(sp3)-H or C(sp3)-H/C(sp3)-H Bonds
    Wei, Wan-Xu
    Czajkowski, Mateusz
    Kuang, Yangjin
    Nguyen, Tu-Anh V.
    Qin, Bo
    Tomanik, Martin
    ACS CATALYSIS, 2024, 14 (09) : 6535 - 6546
  • [47] Palladium-Catalyzed Arylation of Unactivated y-Methylene C(sp3) H and δ-C H Bonds with an Oxazoline-Carboxylate Auxiliary
    Ling, Peng-Xiang
    Fang, Sheng-Long
    Yin, Xue-Song
    Chen, Kai
    Sun, Bo-Zheng
    Shi, Bing-Feng
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (48) : 17503 - 17507
  • [48] Mechanistic Details of the Pd-catalyzed and MPAA Ligand-Enabled β-C(sp3)-H Acetoxylation of Free Carboxylic Acid
    Xu, Li-Ping
    Li, Na
    Musaev, Djamaladdin G. G.
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (02)
  • [49] Palladium(II)-Catalyzed Directed Trifluoromethylthiolation of Unactivated C(sp3)-H Bonds
    Xiong, Heng-Ying
    Besset, Tatiana
    Cahard, Dominique
    Pannecoucke, Xavier
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (08) : 4204 - 4212
  • [50] Synthesis of β-alkynyl α-amino acids via palladium-catalyzed alkynylation of unactivated C(sp3)-H bonds
    Bo Wang
    Gang He
    Gong Chen
    Science China Chemistry, 2015, 58 : 1345 - 1348
12345