Rh(III)-Catalyzed Oxidative C-H Activation/Annulation of Salicylaldehydes with Masked Enynes for the Synthesis of Chromones

被引：4
|
作者：
Li, Bo [1 ,2 ]
Zhu, Jianping [1 ,2 ]
Zheng, Xia [1 ,2 ]
Ti, Wenqing [1 ,2 ]
Huang, Yue [3 ]
Yao, Hequan [1 ,2 ]
机构：
[1] China Pharmaceut Univ, State Key Lab Nat Med SKLNM, Nanjing 210009, Peoples R China
[2] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 210009, Peoples R China
[3] China Pharmaceut Univ, Sch Sci, Dept Organ Chem, Nanjing 210009, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 01期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; ANTIANAPHYLACTIC AGENTS; CATALYZED ALKENE; RHODIUM; CLEAVAGE; ALKYNES; ANNULATION; ALDEHYDES; HYDROACYLATION; CYCLOPROPENES;
D O I：
10.1021/acs.joc.2c02557
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rhodium(III)-catalyzed oxidative C-H activation/annulation of salicylaldehydes with propargylic acetates has been developed for the regioselective synthesis of 3-vinyl chromones in good yields with broad functional group tolerance. 3-Vinyl chromones were converted into biologically active benzo[c]xanthone by I2-mediated oxidative electrocyclization.
引用
收藏
页码：548 / 558
页数：11
相关论文
共 50 条
  • [31] Rh(III)-Catalyzed [3+2] Annulation and C-H Alkenylation of Indoles with 1,3-Diynes by C-H Activation
    Kumar, Sanjeev
    Nunewar, Saiprasad
    Usama, Khan Mohammad
    Kanchupalli, Vinaykumar
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (15) : 2223 - 2229
  • [32] Ru(II)- or Rh(III)-Catalyzed Annulation of Aromatic/Vinylic Acids withAlkylidenecyclopropanes via C-H Activation
    Ramesh, Balu
    Jeganmohan, Masilamani
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (09) : 5668 - 5681
  • [33] One-Pot Synthesis of Highly Substituted Polyheteroaromatic Compounds by Rhodium(III)-Catalyzed Multiple C-H Activation and Annulation
    Jayakumar, Jayachandran
    Parthasarathy, Kanniyappan
    Chen, Yi-Hsiang
    Lee, Tai-Hua
    Chuang, Shih-Ching
    Cheng, Chien-Hong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (37) : 9889 - 9892
  • [34] Rh(III)-catalyzed C-H activation/[4+3] cycloaddition of benzamides and vinylcarbenoids: facile synthesis of azepinones
    Cui, Sunliang
    Zhang, Yan
    Wang, Dahai
    Wu, Qifan
    CHEMICAL SCIENCE, 2013, 4 (10) : 3912 - 3916
  • [35] Rh(III)-Catalyzed synthesis of sultones through C-H activation directed by a sulfonic acid group
    Qi, Zisong
    Wang, Mei
    Li, Xingwei
    CHEMICAL COMMUNICATIONS, 2014, 50 (68) : 9776 - 9778
  • [36] Rh(III)-Catalyzed Synthesis of Isocoumarins via C-H Activation of Phenacyl Phosphoniums with Iodonium Ylides
    Jiang, Lu
    Gao, Lei
    Li, Xiaofei
    Shao, Tingting
    Yao, Jinzhong
    Miao, Maozhong
    Zhou, Hongwei
    SYNTHESIS-STUTTGART, 2024, 56 (01): : 47 - 54
  • [37] Ruthenium-catalyzed oxidative alkyne annulation by C-H activation on ketimines
    Li, Jie
    Ackermann, Lutz
    TETRAHEDRON, 2014, 70 (20) : 3342 - 3348
  • [38] One-Pot Rh(III)-Catalyzed Twofold C-H Activation/Oxidative Annulation of N-Arylpyrroles with Alkynes to Fluorescent Ullazines
    Otero-Riesgo, Sergio
    Varela, Jesus A.
    Saa, Carlos
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (10) : 2312 - 2323
  • [39] Isatoic anhydride as a masked directing group and internal oxidant for Rh(III)-catalyzed decarbonylative annulation through C-H activation: insights from DFT calculations
    Luo, Yanshu
    Zhang, Maosheng
    Xia, Yuanzhi
    CHEMICAL COMMUNICATIONS, 2024, 60 (87) : 12770 - 12773
  • [40] Recent Advances in [Cp*MIII] (M = Co, Rh, Ir)-Catalyzed Intramolecular Annulation Through C-H Activation
    Peneau, Augustin
    Guillou, Catherine
    Chabaud, Laurent
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (42) : 5777 - 5794
12345