Recent advances of propiolic acids in organic reactions

被引:30
作者
Chen, Chuanli [1 ]
Wu, Jinjing [1 ]
Yan, Guobing [1 ]
Huang, Dayun [1 ]
机构
[1] Lishui Univ, Dept Chem, 1 Xueyuan Rd, Lishui City 323000, Zhejiang, Peoples R China
关键词
Mechanism; Decarboxylative; Nucleophile; Electrophilie; ALKYNYL CARBOXYLIC-ACIDS; DECARBOXYLATIVE COUPLING REACTIONS; ONE-POT SYNTHESIS; DIASTEREOSELECTIVE TOTAL-SYNTHESIS; UGI INTRAMOLECULAR HYDROARYLATION; H-PHOSPHINE OXIDES; MICROWAVE-ASSISTED SYNTHESIS; DIVERSITY-ORIENTED SYNTHESIS; CATALYZED DIRECT SYNTHESIS; METAL-FREE APPROACH;
D O I
10.1016/j.tetlet.2019.151415
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, recent advances of propiolic acids in decade (2009-2019) were summarized as five pathways according to their triggered mechanisms: (1) acids as nucleophiles; (2) electrophilic alkynes; (3) decarboxylative coupling; (4) decarboxylative addition; (5) electrophilic acids. Reactions with alkenes, alkynes, isocyanides, indonium, free radicals, R-X (X = leaving groups) et al were discussed. We hope this review will promote future research in this area. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页数:16
相关论文
共 239 条
  • [51] A Gold-Catalyzed Domino Cyclization Enabling Rapid Construction of Diverse Polyheterocyclic Frameworks
    He, Yi
    Li, Zhenghua
    Robeyns, Koen
    Van Meervelt, Luc
    Van der Eycken, Erik V.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (01) : 272 - 276
  • [52] Gold-catalyzed diastereoselective domino dearomatization/ipso-cyclization/aza-Michael sequence: a facile access to diverse fused azaspiro tetracyclic scaffolds
    He, Yi
    Li, Zhenghua
    Tian, Guilong
    Song, Liangliang
    Van Meervelt, Luc
    Van der Eycken, Erik V.
    [J]. CHEMICAL COMMUNICATIONS, 2017, 53 (48) : 6413 - 6416
  • [53] Copper-mediated trifluoromethylation of propiolic acids: facile synthesis of α-trifluoromethyl ketones
    He, Zhengbiao
    Zhang, Rui
    Hu, Mingyou
    Li, Lingchun
    Ni, Chuanfa
    Hu, Jinbo
    [J]. CHEMICAL SCIENCE, 2013, 4 (09) : 3478 - 3483
  • [54] Nickel-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylates with Aryl Tosylates and Mesylates
    Howard, Anna
    Klemann, Samantha
    Kolling, Sarah
    Little, Katrina
    Plasek, Erin
    Kalyani, Dipannita
    [J]. SYNTHESIS-STUTTGART, 2019, 51 (07): : 1603 - 1610
  • [55] Copper-Catalyzed Decarboxylative C-P Cross-Coupling of Alkynyl Acids with H-Phosphine Oxides: A Facile and Selective Synthesis of (E)-1-Alkenylphosphine Oxides
    Hu, Gaobo
    Gao, Yuxing
    Zhao, Yufen
    [J]. ORGANIC LETTERS, 2014, 16 (17) : 4464 - 4467
  • [56] Copper-Catalyzed C-P Coupling through Decarboxylation
    Hu, Jie
    Zhao, Ning
    Yang, Bin
    Wang, Ge
    Guo, Li-Na
    Liang, Yong-Min
    Yang, Shang-Dong
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (20) : 5516 - 5521
  • [57] Ugi Reaction Followed by Intramolecular Diels-Alder Reaction and Elimination of HCl: One-Pot Approach to Arene-Fused Isoindolinones
    Huang, Jianjun
    Du, Xiaochen
    Van Hecke, Kristof
    Van der Eycken, Erik V.
    Pereshivko, Olga P.
    Peshkov, Vsevolod A.
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (30) : 4379 - 4388
  • [58] Switch of Selectivity in the Synthesis of α-Methylene-γ-Lactones: Palladium-Catalyzed Intermolecular Carboesterification of Alkenes with Alkynes
    Huang, Liangbin
    Wang, Qian
    Liu, Xiaohang
    Jiang, Huanfeng
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (23) : 5696 - 5700
  • [59] Palladium-Catalyzed Oxidative Aminocarbonylation by Decarboxylative Coupling: Synthesis of Alkynyl Amides
    Hwang, Jinil
    Choi, Jinseop
    Park, Kyungho
    Kim, Wonyoung
    Song, Kwang Ho
    Lee, Sunwoo
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (10) : 2235 - 2243
  • [60] Palladium-Catalyzed Decarboxylative Trifluoroethylation of Aryl Alkynyl Carboxylic Acids
    Hwang, Jinil
    Park, Kyungho
    Choe, Juseok
    Min, Hongkeun
    Song, Kwang Ho
    Lee, Sunwoo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (07) : 3267 - 3271