Palladium-Catalyzed Synthesis of Carbo- and Heterocycles through Norbornene-Mediated ortho C-H Functionalization

被引:73
作者
Ferraccioli, Raffaella [1 ]
机构
[1] CNR, ISTM, I-20133 Milan, Italy
来源
SYNTHESIS-STUTTGART | 2013年 / 45卷 / 05期
关键词
palladacycle; norbornene; C-H arylation; C-H alkylation; polycycles; ALKYLATION-ALKENYLATION REACTIONS; TETRASUBSTITUTED HELICAL ALKENES; SUBSTITUTED ARYL IODIDES; CROSS-COUPLING REACTIONS; NITROGEN-CONTAINING HETEROCYCLES; ONE-STEP SYNTHESIS; DIRECT ARYLATION; STEREOSELECTIVE-SYNTHESIS; EXPEDITIOUS SYNTHESIS; BOND FORMATION;
D O I
10.1055/s-0032-1318218
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Direct aromatic functionalization based on the use of a palladium catalyst and norbornene is a useful method to achieve straightforward synthesis of carbo- and heterocyclic compounds. New ring formation occurs through a cascade process triggered by ortho C-H alkylation (inter- and intramolecular) or arylation (homo- and heterocoupling) of aryl iodides. Up to four new carbon-carbon bonds are generated under palladium control in a single operation.
引用
收藏
页码:581 / 591
页数:11
相关论文
共 50 条
  • [1] Recent Developments in the Palladium-Catalyzed/Norbornene-Mediated Synthesis of Carbo- and Heterocycles
    Patel, Monak
    Desai, Bhargav
    Ramani, Arti
    Dholakiya, Bharatkumar Z.
    Naveen, Togati
    CHEMISTRYSELECT, 2021, 6 (31): : 8085 - 8106
  • [2] Synthesis in the Key of Catellani: Norbornene-Mediated ortho C-H Functionalization
    Martins, Andrew
    Mariampillai, Brian
    Lautens, Mark
    C-H ACTIVATION, 2010, 292 : 1 - 33
  • [3] Palladium-catalyzed Synthesis of Fused Carbo- and Heterocycles
    Ghosh, Tapas
    Biswas, Diptam
    Bhakta, Sayantika
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (21)
  • [4] Palladium-catalysed norbornene-mediated C-H functionalization of arenes
    Ye, Juntao
    Lautens, Mark
    NATURE CHEMISTRY, 2015, 7 (11) : 863 - 870
  • [5] Palladium-Catalyzed/Norbornene-Mediated C-H Activation/N-Tosylhydrazone Insertion Reaction: A Route to Highly Functionalized Vinylarenes
    Zhou, Ping-Xin
    Zheng, Lan
    Ma, Jun-Wei
    Ye, Yu-Ying
    Liu, Xue-Yuan
    Xu, Peng-Fei
    Liang, Yong-Min
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (22) : 6745 - 6751
  • [6] Palladium-catalyzed and norbornene-mediated C-H amination and C-O alkenylation of aryl triflates
    Zhang, Shuo
    Yang, Lei
    Fu, Jianbin
    Tan, Qihang
    Liu, Kuan
    Huang, Tianzeng
    Li, Chunya
    Liu, Long
    Chen, Tieqiao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (21) : 4398 - 4403
  • [7] Synthesis of Biindolizines through Highly Regioselective Palladium-Catalyzed C-H Functionalization
    Xia, Ji-Bao
    Wang, Xue-Qiang
    You, Shu-Li
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (01) : 456 - 458
  • [8] Palladium-Catalyzed Direct 2-Alkylation of Indoles by Norbornene-Mediated Regioselective Cascade C-H Activation
    Jiao, Lei
    Bach, Thorsten
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) : 12990 - 12993
  • [9] An Electrophilic Approach to the Palladium-Catalyzed Carbonylative C-H Functionalization of Heterocycles
    Tjutrins, Jevgenijs
    Arndtsen, Bruce A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (37) : 12050 - 12054
  • [10] Palladium-Catalyzed Norbornene-Mediated Tandem Amination/Cyanation Reaction: A Method for the Synthesis of ortho-Aminated Benzonitriles
    Luo, Bo
    Gao, Jin-Ming
    Lautens, Mark
    ORGANIC LETTERS, 2016, 18 (17) : 4166 - 4169