Pd-Catalyzed Regioselective Oxidative C–H Functionalization of Substituted Imidazo[1,2-a]quinoline: Structural Characterization of Binuclear Cyclometalated Intermediates

被引:0
|
作者
Mithun Sarkar
Jitendra K. Bera
机构
[1] Indian Institute of Technology Kanpur,Department of Chemistry
来源
Proceedings of the National Academy of Sciences, India Section A: Physical Sciences | 2014年 / 84卷
关键词
Regioselective C–H functionalization; Bimetallic catalysis; Oxidative addition; Reductive elimination; Cyclometalation;
D O I
暂无
中图分类号
学科分类号
摘要
Reaction of 4-phenylimidazo[1,2-a]quinoline with one and more than two equivalents of PhI(OAc)2 afforded regioselective mono- and bis-acetoxylated products respectively in presence of catalytic amount of Pd(OAc)2. Stoichiometric reaction between imidazo–quinoline ligand and Pd(OAc)2 gave an acetate bridged binuclear cyclometalated complex 1. X-ray structure confirmed selective cyclometalation at ortho position of the phenyl ring. Furthermore, a formamidinate analogue, 2 is obtained by replacing the bridging acetates in 1.
引用
收藏
页码:227 / 234
页数:7
相关论文
共 50 条
  • [1] Pd-Catalyzed Regioselective Oxidative C-H Functionalization of Substituted Imidazo[1,2-a] quinoline: Structural Characterization of Binuclear Cyclometalated Intermediates
    Sarkar, Mithun
    Bera, Jitendra K.
    PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES INDIA SECTION A-PHYSICAL SCIENCES, 2014, 84 (02) : 227 - 234
  • [2] Pd-catalyzed oxidative cross-coupling of imidazo[1,2-a]pyridine with arenes
    Wang, Shaohua
    Liu, Wenjie
    Cen, Jinghe
    Liao, Jinqiang
    Huang, Jianping
    Zhan, Haiying
    TETRAHEDRON LETTERS, 2014, 55 (09) : 1589 - 1592
  • [3] Highly regioselective C-H bond functionalization: palladium-catalyzed arylation of substituted imidazo[1,2-a]pyridine with aryl chlorides
    Cao, Hua
    Lin, Yuanguang
    Zhan, Haiying
    Du, Zuodong
    Lin, Xiulian
    Liang, Qi-Mei
    Zhang, Hong
    RSC ADVANCES, 2012, 2 (14) : 5972 - 5975
  • [4] Pd/Cu-Catalyzed Oxidative C-H Alkenylation of Imidazo[1,2-a]pyridines
    Koubachi, Jamal
    Berteina-Raboin, Sabine
    Mouaddib, Abderrahim
    Guillaumet, Gerald
    SYNTHESIS-STUTTGART, 2009, (02): : 271 - 276
  • [5] Electrochemical Oxidative Regioselective C-H Cyanation of Imidazo[1,2-a]pyridines
    Cui, Ting
    Zhan, Yanling
    Dai, Changhui
    Lin, Jun
    Liu, Ping
    Sun, Peipei
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (22): : 15897 - 15905
  • [6] Pd-Catalyzed Aerobic C-H Carbonylative Esterification of Imidazo[1,2-a]pyridines with Alcohols as the Carbonyl Source
    Sun, Jiapeng
    Luo, Hanxiao
    Wang, Junyong
    Li, Hongliang
    Zheng, Raorao
    Qiao, Dingru
    Zhao, Jiaji
    Yu, Yue
    Cao, Hua
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (13): : 4704 - 4713
  • [7] Palladium(II)-catalyzed intermolecular oxidative C-3 alkenylations of imidazo[1,2-a]pyridines by substrate-contolled regioselective C-H functionalization
    Cao, Hua
    Lei, Sai
    Liao, Jinqiang
    Huang, Jianping
    Qiu, Huifang
    Chen, Qinlin
    Qiu, Shuxian
    Chen, Yaoyi
    RSC ADVANCES, 2014, 4 (91) : 50137 - 50140
  • [8] Pd-Catalyzed direct C-H arylation of pyrrolo[1,2-a]quinoxalines
    Hao, Di
    Yang, Zhen
    Liu, Yali
    Li, Yang
    Li, Chuntian
    Gu, Yanlong
    Vaccaro, Luigi
    Liu, Jichang
    Liu, Ping
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (04) : 847 - 851
  • [9] Highly regioselective C-H bond functionalization of imidazo[1,2-a]pyridines with aryl halides catalyzed by Ru-arene complex
    Yang, Hai
    Yang, Liping
    Li, Yuan
    Zhang, Fan
    Liu, Huajie
    Yi, Bing
    CATALYSIS COMMUNICATIONS, 2012, 26 : 11 - 14
  • [10] Copper-Catalyzed Intermolecular Oxidative Cyclization of Haloalkynes: Synthesis of 2-Halo-substituted Imidazo[1,2-a]pyridines, Imidazo[1,2-a]pyrazines and Imidazo[1,2-a]pyrimidines
    Gao, Yang
    Yin, Meizhou
    Wu, Wanqing
    Huang, Huawen
    Jiang, Huanfeng
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (11-12) : 2263 - 2273