Cu-catalyzed decarboxylative coupling of propiolic acids with boronic acids

被引：29
|
作者：
Shi, Leilei [1 ,2 ]
Jia, Wei [2 ]
Li, Xun [1 ]
Jiao, Ning [2 ,3 ]
机构：
[1] Shandong Univ, Sch Pharmaceut Sci, Minist Educ, Key Lab Chem Biol, Jinan 250012, Shandong, Peoples R China
[2] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
[3] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 15期
基金：
美国国家科学基金会;
关键词：
Decarboxylative coupling; Propiolic acids; Boronic acids; Unsymmetrical alkynes; ALKYNYL CARBOXYLIC-ACIDS; TERMINAL ALKYNES; ARYL HALIDES; VINYL HALIDES; SONOGASHIRA REACTION; CROSS-COUPLINGS; PALLADIUM-FREE; IODIDES; HALODECARBOXYLATION; EFFICIENT;
D O I：
10.1016/j.tetlet.2013.01.118
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A mild procedure of Cu-catalyzed decarboxylative cross-coupling of aryl- and alkynyl-boronic acids for construction of unsymmetrical substituted alkynes has been developed. The usage of inexpensive copper chloride as catalyst, and employing stable alkynl carboxylic acids and boronic acids as the substrates under oxidative conditions for sp-sp(2) coupling, make this method very easy to operate. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1951 / 1955
页数：5
相关论文
共 50 条
  • [21] Transition-metal-free Csp3-Csp doubly decarboxylative coupling of amino acids and propiolic acids
    Hu, Junduo
    Liu, Leyan
    Wang, Haixiang
    Huang, Liliang
    Gao, Huanmei
    Feng, Huangdi
    SUSTAINABLE CHEMISTRY AND PHARMACY, 2024, 38
  • [22] Chemodivergent Synthesis of Oxazolidin-2-ones via Cu-Catalyzed Carboxyl Transfer Annulation of Propiolic Acids with Amines
    Xie, Yujuan
    Feng, Huangdi
    Qi, Yayu
    Huang, Junhai
    Huang, Liliang
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (23): : 16940 - 16947
  • [23] Copper-catalyzed direct decarboxylative hydrosulfonylation of aryl propiolic acids with sulfonylhydrazides leading to vinylsulfones
    Li, Siyu
    Li, Xiang
    Yang, Fan
    Wu, Yangjie
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09): : 1076 - 1079
  • [24] Cu-Catalyzed Asymmetric Difluoromethylation of Amino Acids with Difluorocarbene
    Lin, Jinhong
    Xiao, Jichang
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (08) : 3346 - 3348
  • [25] Palladium-Catalyzed Decarboxylative Homodimerization of Propiolic Acids: Synthesis of 1,3-Enynes
    Seo, Eunkyeong
    Oh, Jonghoon
    Lee, Sunwoo
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2021, 42 (03) : 514 - 516
  • [26] Switching of Enantioselectivity in the Cu-Catalyzed Asymmetric Decarboxylative Aldol Reaction of Tryptanthrin with β-Keto Acids: An Unexpected Counteranion Effect
    Feng, Fang-Fang
    Wang, Xue-Qi
    Sun, Long
    Cheung, Chi Wai
    Nie, Jing
    Ma, Jun-An
    ORGANIC LETTERS, 2021, 23 (11) : 4379 - 4384
  • [27] Decarboxylative dipropargylation of primary amines with propiolic acids and formaldehyde via metal-free coupling
    Jia, Huihui
    Feng, Huangdi
    Sun, Zhihua
    TETRAHEDRON, 2015, 71 (18) : 2724 - 2728
  • [28] Cu-Catalyzed Oxidative Allylic C-H Arylation of Inexpensive Alkenes with (Hetero)Aryl Boronic Acids
    Pal, Suman
    Cotard, Marine
    Gerardin, Baptiste
    Hoarau, Christophe
    Schneider, Cedric
    ORGANIC LETTERS, 2021, 23 (08) : 3130 - 3135
  • [29] Rhodium(I)-Catalyzed Defluorinative Coupling of Boronic Acids with Monofluoroalkenes
    Zong, Yuwei
    Tang, Yihan
    Tsui, Gavin Chit
    ORGANIC LETTERS, 2022, 24 (35) : 6380 - 6385
  • [30] Cu-catalyzed decarboxylative iodination of aryl carboxylic acids with NaI: A practical entry to aryl iodides under aerobic conditions
    Fu, Zhengjiang
    Jiang, Yongqing
    Jiang, Ligao
    Li, Zhaojie
    Guo, Shengmei
    Cai, Hu
    TETRAHEDRON LETTERS, 2018, 59 (51) : 4458 - 4461
12345