Nickel(0)-Catalyzed Decarbonylative Cross-Coupling of Aromatic Esters with Arylboronic Acids via Chelation Assistance

被引:0
|
作者
Hu, Zhenzhu [1 ]
Wang, Yuhang [1 ]
Ma, Peng [1 ]
Wu, Xiaqian [1 ]
Wang, Jianhui [2 ,3 ]
机构
[1] Tianjin Univ, Dept Chem, Coll Sci, Tianjin 300350, Peoples R China
[2] Tianjin Univ, Dept Chem, Coll Sci, Tianjin 300350, Peoples R China
[3] Tianjin Univ, Inst Mol Plus, Tianjin 300350, Peoples R China
来源
ACS OMEGA | 2022年 / 7卷 / 25期
基金
中国国家自然科学基金;
关键词
C-O ACTIVATION; CARBOXYLIC ANHYDRIDES; CATALYZED ADDITION; BOND-CLEAVAGE; BORONIC ACIDS; NICKEL; ARYLATION; CONSTRUCTION; DERIVATIVES; ARYLKETONES;
D O I
10.1021/acsomega.2c0110521537ACSOmega2022
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
10-Arylbenzo[h]quinolines were synthesized by cross-coupling of ethyl benzo[h]quinoline-10-carboxylate with arylboronic acids via group-directed Ni(0) catalyzation. The catalytic system combining Ni(COD)2 (10 mol %) with PCy3 (20 mol %) and t-BuOK (3 equiv) was optimal for the above transformations. A series of arylboronic acids reacted with ethyl benzo[h]quinoline-10-carboxylates for the production of various substituted 10-phenyl[h]quinolines in moderate and good yields under optimized reaction conditions.
引用
收藏
页码:21537 / 21545
页数:9
相关论文
共 50 条
  • [31] Palladium-catalyzed cross-coupling of aryldiazonium tetrafluoroborate salts with arylboronic esters
    Willis, DM
    Strongin, RM
    TETRAHEDRON LETTERS, 2000, 41 (33) : 6271 - 6274
  • [32] Pd-catalyzed Suzuki cross-coupling reactions of glycerol arylboronic esters
    Nichele, Tatiana Z.
    Favero, Cristiano
    Monteiro, Adriano L.
    CATALYSIS COMMUNICATIONS, 2009, 10 (05) : 693 - 696
  • [33] Cobalt-Catalyzed Cross-Coupling Reactions of Arylboronic Esters and Aryl Halides
    Duong, Hung A.
    Wu, Wenqin
    Teo, Yu-Yuan
    ORGANOMETALLICS, 2017, 36 (22) : 4363 - 4366
  • [34] Chelation assistance in the activation of Csp3-S bonds in nickel-catalyzed cross-coupling reactions
    Wong, K.-T.
    Yuan, T.-M.
    Wang, M.C.
    Tung, H.-H.
    Luh, T.-Y.
    Journal of the American Chemical Society, 1994, 116 (20):
  • [35] CHELATION ASSISTANCE IN THE ACTIVATION OF C(SP(3))-S BONDS IN NICKEL-CATALYZED CROSS-COUPLING REACTIONS
    WONG, KT
    YUAN, TM
    WANG, MC
    TUNG, HH
    LUH, TY
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) : 8920 - 8929
  • [36] Facile synthesis of substituted alkynes by cyclopalladated ferrocenylimine catalyzed cross-coupling of arylboronic acids/esters with terminal alkynes
    Yang, Fan
    Wu, Yangjie
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (21) : 3476 - 3479
  • [37] Palladium-catalyzed decarboxylative cross-coupling of alkynyl carboxylic acids with arylboronic acids
    Feng, Chao
    Loh, Teck-Peng
    CHEMICAL COMMUNICATIONS, 2010, 46 (26) : 4779 - 4781
  • [38] Decarbonylative Reductive Coupling of Aromatic Esters by Nickel and Palladium Catalyst
    Peng, Yunfei
    Isshiki, Ryota
    Muto, Kei
    Yamaguchi, Junichiro
    CHEMISTRY LETTERS, 2022, 51 (07) : 749 - 753
  • [39] Synthesis of Biaryls via Decarbonylative Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling of Aryl Anhydrides
    Zhou, Jing-Ya
    Liu, Rui-Qing
    Wang, Cheng-Yi
    Zhu, Yong-Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (21): : 14149 - 14157
  • [40] A Thioether-Catalyzed Cross-Coupling Reaction of Allyl Halides and Arylboronic Acids
    Xu, Jingwei
    He, Zhiqi
    Zhang, Jiwei
    Chen, Jiean
    Huang, Yong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (43)