Application of Palladium-Catalyzed C(sp2)-H Bond Arylation to the Synthesis of Polycyclic (Hetero)Aromatics

被引:116
|
作者
Hagui, Wided [1 ]
Doucet, Henri [1 ]
Soule, Jean-Francois [1 ]
机构
[1] Univ Rennes, CNRS, ISCR UMR 6226, F-35000 Rennes, France
来源
CHEM | 2019年 / 5卷 / 08期
关键词
ANNULATIVE PI-EXTENSION; HIGHLY EFFICIENT ROUTE; O-BROMOBENZYL ALCOHOLS; BOWL-SHAPED FRAGMENTS; H DUAL ACTIVATION; ONE-POT SYNTHESIS; AROMATIC-HYDROCARBONS; C-C; STRUCTURAL-ANALYSIS; BENZENESULFONYL CHLORIDES;
D O I
10.1016/j.chempr.2019.06.005
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Recently, the use of the palladium-catalyzed inter- and/or intra-molecular C-H bond arylations in the building of various pi-extended (hetero)aromatic structures has emerged as a suitable alternative to the previous multi-step synthesis. This new methodology even allowed for the preparation of unprecedented pi-extended molecules owing to perfect control of the reaction sites. This review gives an overview of various syntheses of polycyclic aromatic hydrocarbons (PAHs) and polycyclic heteroaromatics (PCHs) with planar, bowl-shaped, and helical structures prepared in high efficiency and selectivity via Palladium-catalyzed C-H bond arylations.
引用
收藏
页码:2006 / 2078
页数:73
相关论文
共 50 条
  • [1] Oxalyl Amide Assisted Palladium-Catalyzed Arylation of C(sp2)-H Bond at the δ Position
    Han, Jian
    Liu, Pei
    Wang, Chao
    Wang, Qian
    Zhang, Jingyu
    Zhao, Yanwei
    Shi, Daqing
    Huang, Zhibin
    Zhao, Yingsheng
    ORGANIC LETTERS, 2014, 16 (21) : 5682 - 5685
  • [2] Palladium-Catalyzed sp2 C-H Arylation of Azoarenes with Arylhydrazines
    Li, Mingyang
    Ye, Yong
    CHEMCATCHEM, 2015, 7 (24) : 4137 - 4142
  • [3] Palladium-Catalyzed C(sp2)-H Arylation of Peptides Directed by Aspartic Acid
    Weng, Yiyi
    Zhan, Xuecheng
    Zhang, Yiyang
    Lin, Wen
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (04): : 2334 - 2343
  • [4] Palladium-Catalyzed Ortho-Arylation of Benzamides via Direct sp2 C-H Bond Activation
    Li, Dan-Dan
    Yuan, Ting-Ting
    Wang, Guan-Wu
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07): : 3341 - 3347
  • [5] Fully Substituted Pyrazoles Assisted Palladium-Catalyzed Late-Stage Arylation of C(sp2)-H Bond
    Fu, Xiaopan
    Wang, Yangyang
    Yang, Jinyue
    Wu, Gaorong
    Xia, Chengcai
    Ji, Yafei
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (12) : 4305 - 4314
  • [6] Palladium-Catalyzed C(sp2)-H Arylation Using Formamide as a Transformable Directing Group
    Wan, Congqing
    Zhao, Jiaji
    Xu, Mingfang
    Huang, Jinbo
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (10): : 4751 - 4756
  • [7] Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Aldehydes
    Basle, Olivier
    Bidange, Johan
    Shuai, Qi
    Li, Chao-Jun
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (07) : 1145 - 1149
  • [8] Palladium-Catalyzed Oxidative sp2 C-H Bond Acylation with Alcohols
    Xiao, Fuhong
    Qi Shuai
    Zhao, Feng
    Basle, Olivier
    Deng, Guojun
    Li, Chao-Jun
    ORGANIC LETTERS, 2011, 13 (07) : 1614 - 1617
  • [9] Enantioselective palladium-catalyzed C(sp2)-H carbamoylation
    Dong, Wenfeng
    Xu, Guangqing
    Tang, Wenjun
    TETRAHEDRON, 2019, 75 (24) : 3239 - 3247
  • [10] Synthesis of modified bile acids via palladium-catalyzed C(sp3)-H (hetero)arylation
    Borade, Somnath Arjun
    Naharwal, Sushma
    Bhambri, Himanshi
    Mandal, Sanjay K.
    Bajaj, Kiran
    Chitkara, Deepak
    Sakhuja, Rajeev
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (33) : 6719 - 6729