Palladium-Catalyzed [3+2] Annulation of ortho-Substituted Iodoarenes with Maleimides via a Consecutive Double Heck-type Strategy

被引:6
|
作者
Naveen, Jakkula [1 ]
Satyanarayana, Gedu [1 ]
机构
[1] Indian Inst Technol IIT Hyderabad, Dept Chem, Sangareddy 502284, Telangana, India
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 23期
关键词
ONE-POT SYNTHESIS; C-H ALKYLATION; ACTIVATION; CYCLIZATION; ACCESS; ARYL; CARBOPALLADATION; HALIDES;
D O I
10.1021/acs.joc.3c01703
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we report an efficient [3 + 2] annulation of ortho-substituted iodoarenes with maleimides via a palladium-catalyzed consecutive double Heck-type strategy, leading to fused tricyclic frameworks of pharmaceutical relevance. The protocol ensued through consecutive inter- and intramolecular Heck couplings effectively. This approach was compatible with a large variety of substrates and functional groups, and it was remarkably tolerated with unprotected maleimide.
引用
收藏
页码:16229 / 16247
页数:19
相关论文
共 50 条
  • [31] Enantioselective Construction of Highly Substituted Pyrrolidines by Palladium-Catalyzed Asymmetric [3+2] Cycloaddition of Trimethylenemethane with Ketimines
    Trost, Barry M.
    Silverman, Steven M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (24) : 8238 - +
  • [32] Highly Substituted Enantioenriched Cyclopentane Derivatives by Palladium-Catalyzed [3+2] Trimethylenemethane Cycloadditions with Disubstituted Nitroalkenes
    Trost, Barry M.
    Bringley, Dustin A.
    O'Keefe, B. Michael
    ORGANIC LETTERS, 2013, 15 (22) : 5630 - 5633
  • [33] DFT Study on the Mechanism of the Palladium-Catalyzed [3+2] Annulation of Aromatic Amides with Maleimides via Benzylic and meta-C-H Bond Activation: Role of the External Ligand Ac-Gly-OH
    Li, Guorong
    Shang, Zhenfeng
    Li, Ruifang
    Xu, Xiufang
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 89 (02): : 1228 - 1234
  • [34] Palladium-Catalyzed Synthesis of Substituted Phenanthrenes via a C-H Annulation of 2-Biaryl Triflates with Alkynes
    Prabhakaran, Mohan
    Parthasarathy, Kanniyappan
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (22): : 16363 - 16374
  • [35] Palladium-Catalyzed Oxidative Difunctionalization of Alkenes with α-Carbonyl Alkyl Bromides Initiated through a Heck-type Insertion: A Route to Indolin-2-ones
    Fan, Jian-Hong
    Wei, Wen-Ting
    Zhou, Ming-Bo
    Song, Ren-Jie
    Li, Jin-Heng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (26) : 6650 - 6654
  • [36] Synergistic N-Heterocyclic Carbene/Palladium-Catalyzed [3+2] Annulation of Vinyl Enolates with 1-Tosyl-2-vinylaziridine
    Gao, Jian
    Zhang, Jianming
    Fang, Shuaishuai
    Feng, Jie
    Lu, Tao
    Du, Ding
    ORGANIC LETTERS, 2020, 22 (19) : 7725 - 7729
  • [37] PALLADIUM-CATALYZED [3+2] ANNULATION OF meso-BROMOPORPHYRINS WITH SILYLACETYLENES AND DESILYLATION OF 8a-SILYL-7,8-DEHYDROPURPURIN
    Fukui, Norihito
    Arai, Seiji
    Shinokubo, Hiroshi
    Yorimitsu, Hideki
    Osuka, Atsuhiro
    HETEROCYCLES, 2015, 90 (01) : 252 - 260
  • [38] Palladium-Catalyzed (3+2) Annulation of Aromatic Acids by C(sp3)-H Olefination and Decarboxylative Cross-Coupling Reaction
    Xu, Xiaobo
    Wang, Yangyang
    Yu, Xiao
    Liu, Xian
    Hao, Liqiang
    Ji, Yafei
    ORGANIC LETTERS, 2024, 26 (07) : 1338 - 1342
  • [39] Palladium-Catalyzed [3+2] Annulation of Aryl Halides with 7-Oxa- and 7-Azabenzonorbornadienes via C(sp2 or sp3)-H Activation
    Li, Xiaojiao
    Pan, Xianting
    Qi, Zisong
    Li, Xingwei
    ORGANIC LETTERS, 2022, 24 (49) : 8964 - 8968
  • [40] Synthesis of 1-Substituted 2-(Trifluoromethyl)indoles via a Palladium-Catalyzed Double Amination Reaction
    Dong, Shu-Xiang
    Zhang, Xing-Guo
    Liu, Qiong
    Tang, Ri-Yuan
    Zhong, Ping
    Li, Jin-Heng
    SYNTHESIS-STUTTGART, 2010, (09): : 1521 - 1525