C(sp)-C(sp3) Bond Formation through Ligand- and Additive-Free CuO-Mediated Decarboxylative Direct Cross-Coupling of Coumarin-/Chromone-3-carboxylic Acids and Terminal Alkynes

被引:5
|
作者
Bhowmick, Anindita [1 ]
Brahmachari, Goutam [1 ]
机构
[1] Visva Bharati, Dept Chem, Lab Nat Prod & Organ Synth, Santini Ketan 731235, West Bengal, India
关键词
COUMARINS; FUNCTIONALIZATION; ACETYLENES; DESIGN; AGENTS;
D O I
10.1021/acs.orglett.3c02369
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A practical and efficient method for the synthesis of functionalized 4-(aryl-/heteroaryl-ethynyl)chroman-2-ones and 2-(aryl-/heteroaryl-ethynyl)chroman-4-ones through copper-catalyzed decarboxylative direct cross-coupling of coumarin-/chromone-3-carboxylic acids with terminal alkynes, leading to the formation of C(sp)-C(sp(3)) bonds, has been unearthed. Advantages of this protocol include avoidance of any ligands and bases, a broad substrate scope, tolerance of diverse functional groups, and good to excellent yields.
引用
收藏
页码:7095 / 7099
页数:5
相关论文
共 10 条
  • [1] PdII-Catalyzed Enantioselective C(sp3)-H Activation/Cross-Coupling Reactions of Free Carboxylic Acids
    Hu, Liang
    Shen, Peng-Xiang
    Shao, Qian
    Hong, Kai
    Qiao, Jennifer X.
    Yu, Jin-Quan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (07) : 2134 - 2138
  • [2] Multimetallic catalysed radical oxidative C(sp3)-H/C(sp)-H cross-coupling between unactivated alkanes and terminal alkynes
    Tang, Shan
    Wang, Pan
    Li, Haoran
    Lei, Aiwen
    NATURE COMMUNICATIONS, 2016, 7
  • [3] Transition Metal-Free Oxidative Cross-Coupling C(sp2)-C(sp3) Bond Formation: Regioselective C-3 Alkylation of Coumarins with Tertiary Amines
    Dian, Longyang
    Zhang-Negrerie, Daisy
    Du, Yunfei
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (18) : 3090 - 3094
  • [4] Stereospecific Pd-Catalyzed Intermolecular C(sp3)-C(sp) Cross-Coupling of Diarylmethyl Carbonates and Terminal Alkynes Under Base-Free Conditions
    Tabuchi, Sho
    Hirano, Koji
    Miura, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (47) : 16823 - 16827
  • [5] Aryl Acid-Alcohol Cross-Coupling: C(sp3)-C(sp2) Bond Formation from Nontraditional Precursors
    Lin, Eva
    Wang, Johnny Z.
    Mao, Edna
    Tsang, Stephanie
    Carsch, Kurtis M.
    Kullmer, Cesar N. Prieto
    McNamee, Ryan E.
    Long, Jeffrey R.
    Le, Chi
    MacMillan, David W. C.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2025,
  • [6] meso-Methyl Amination of BODIPYs by Regiospecific Cross Dehydrogenative Coupling via Direct C(sp3)-N(sp3) Bond Formation
    Dutta, Kartik
    Wadawale, Amey P.
    Mula, Soumyaditya
    ORGANIC LETTERS, 2024, 26 (35) : 7267 - 7272
  • [7] Metal-Free Direct Alkylation of Ketene Dithioacetals by Oxidative C(sp2)-H/C(sp3)-H Cross-Coupling
    Wen, Jiangwei
    Zhang, Fan
    Shi, Wenyan
    Lei, Aiwen
    CHEMISTRY-A EUROPEAN JOURNAL, 2017, 23 (37) : 8814 - 8817
  • [8] Direct C-C Bond Formation through Decarboxylative Oxidative Cross-Coupling of Cinnamic Acids with Amides under Metal-Free Condition
    Lu, Xiaobiao
    Xiao, Xi
    Wan, Changfeng
    Wang, Zhiyong
    Liu, Jinbiao
    ACTA CHIMICA SINICA, 2021, 79 (06) : 751 - 754
  • [9] Iron-Catalyzed Cross-Dehydrogenative Coupling of Oxindoles with Thiols/Selenols for Direct C(sp3)-S/Se Bond Formation
    Huang, Lu-Shan
    Han, Dong-Yang
    Xu, Da-Zhen
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (17) : 4016 - 4021
  • [10] Molecular iodine mediated oxidative cross-coupling of sp3 C-H with sp2 C-H: direct synthesis of substituted indolo[2,3-b]carbazoles via formal [2+2+1+1] cyclization
    Xue, Wei-jian
    Gao, Qing-He
    Wu, An-xin
    TETRAHEDRON LETTERS, 2015, 56 (51) : 7115 - 7119