Transition-Metal-Free Decarboxylative Coupling Reactions for the Synthesis of Propargyl Alcohols

被引：9
|
作者：
Irudayanathan, Francis Mariaraj [1 ]
Kim, Jimin [1 ]
Song, Kwang Ho [2 ]
Lee, Sunwoo [1 ]
机构：
[1] Chonnam Natl Univ, Dept Chem, Gwangju 61186, South Korea
[2] Korea Univ, Dept Chem & Biol Engn, Seoul 02841, South Korea
来源：
ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 5卷 / 09期
基金：
新加坡国家研究基金会;
关键词：
aldehydes; alkynyl carboxylic acid; decarboxylative coupling; ketones; propargyl alcohol; TRIFLUOROMETHYL KETONES; CATALYTIC ALKYNYLATION; CARBOXYLIC-ACIDS; TERMINAL ALKYNES; ALDEHYDES; EFFICIENT; AMINES; WATER; NANOPARTICLES; HETEROCYCLES;
D O I：
10.1002/ajoc.201600265
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Propargyl alcohols have been directly synthesized by decarboxylative coupling reactions with an alkynyl carboxylic acid and an aldehyde/ketone in the absence of a transition-metal catalyst. When the decarboxylative coupling reaction was conducted with Cs2CO3 in DMSO, the desired propargyl alcohols were formed in good yield. In addition, the reactions with 2,2,2-trifluoroacetophenone and aryl alkynyl carboxylic acids gave trifluoromethylated propargyl alcohols.
引用
收藏
页码：1148 / 1154
页数：7
相关论文
共 50 条
  • [1] Transition-Metal-Free Decarboxylative Photoredox Coupling of Carboxylic Acids and Alcohols with Aromatic Nitriles
    Lipp, Benjamin
    Nauth, Alexander M.
    Opatz, Till
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (15): : 6875 - 6882
  • [2] Transition-Metal-Free Coupling Reactions
    Sun, Chang-Liang
    Shi, Zhang-Jie
    CHEMICAL REVIEWS, 2014, 114 (18) : 9219 - 9280
  • [3] Transition-metal-free Coupling Reactions of Aryl Halides
    Shirakawa, Eiji
    Hayashi, Tamio
    CHEMISTRY LETTERS, 2012, 41 (02) : 130 - 134
  • [4] Arynes in Transition-Metal-Free Multicomponent Coupling Reactions
    Bhojgude, Sachin Suresh
    Biju, Akkattu T.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (07) : 1520 - 1522
  • [5] Transition-metal-free synthesis of vinyl sulfones via tandem cross-decarboxylative/coupling reactions of sodium sulfinates and cinnamic acids
    Xu, Yanli
    Tang, Xiaodong
    Hu, Weigao
    Wu, Wanqing
    Jiang, Huanfeng
    GREEN CHEMISTRY, 2014, 16 (08) : 3720 - 3723
  • [6] Transition-metal-free coupling reactions involving gem -diborylalkanes
    Li, Yongli
    Shen, Dalong
    Zhang, Hao
    Liu, Zhenxing
    CHINESE CHEMICAL LETTERS, 2023, 34 (07)
  • [7] Transition-metal-free Suzuki-type coupling reactions
    Leadbeater, NE
    Marco, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (12) : 1407 - 1409
  • [8] Transition-metal-free coupling reactions involving gem–diborylalkanes
    Yongli Li
    Dalong Shen
    Hao Zhang
    Zhenxing Liu
    ChineseChemicalLetters, 2023, 34 (07) : 43 - 48
  • [9] Transition-Metal-Free Heterobiaryl Synthesis via Aryne Coupling
    Saied, Tarak
    Demangeat, Catherine
    Panossian, Armen
    Leroux, Frederic R.
    Fort, Yves
    Comoy, Corinne
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (31-32) : 5275 - 5284
  • [10] Synthesis of Functionalized Alkenes by a Transition-Metal-Free Zweifel Coupling
    Armstrong, Roly J.
    Niwetmarin, Worawat
    Aggarwal, Varinder K.
    ORGANIC LETTERS, 2017, 19 (10) : 2762 - 2765
12345