Palladium-catalyzed carbonylative synthesis of alkynones from aryl iodides and phenylpropiolic acid employing formic acid as the CO source

被引:14
作者
Li, Chong-Liang [1 ]
Zhang, Wan-Quan [1 ]
Qi, Xinxin [1 ]
Peng, Jin-Bao [1 ]
Wu, Xiao-Feng [1 ,2 ]
机构
[1] Zhejiang Sci Tech Univ, Dept Chem, Xiasha Campus, Hangzhou 310018, Zhejiang, Peoples R China
[2] Univ Rostock, Leibniz Inst Katalyse eV, Albert Einstein Str 29a, D-18059 Rostock, Germany
关键词
Phenylpropiolic acid; Decarboxylation; Carbonylation; Palladium; Formic acid; Alkynones; CARBON-MONOXIDE SOURCE; TERMINAL ALKYNES; COUPLING REACTIONS; REDUCTIVE CARBONYLATION; PYRIMIDINE SYNTHESIS; SONOGASHIRA REACTION; IONIC LIQUIDS; O-IODOPHENOLS; CHLORIDES; CONVENIENT;
D O I
10.1016/j.jorganchem.2017.03.028
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A palladium-catalyzed procedure for the decarboxylative-carbonylation of phenylpropiolic acid with iodobenzenes to the corresponding alkynones with formic acid as carbon monoxide source has been developed. Various alkynones were produced in moderate to good yields. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:9 / 11
页数:3
相关论文
共 55 条
  • [1] Carbonylative Sonogashira coupling of terminal alkynes with aqueous ammonia
    Ahmed, MSM
    Mori, A
    [J]. ORGANIC LETTERS, 2003, 5 (17) : 3057 - 3060
  • [2] Synthesis of ynones by palladium-catalyzed acylation of terminal alkynes with acid chlorides
    Alonso, DA
    Nájera, C
    Pacheco, MC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (05) : 1615 - 1619
  • [3] Pd-catalyzed regioselective hydroarylation of α-(2-aminoaryl)-α,β-ynones with organoboron derivatives as a tool for the synthesis of quinolines:: experimental evidence and quantum-chemical calculations
    Arcadi, Antonio
    Aschi, Massimiliano
    Marinelli, Fabio
    Verdecchia, Mirella
    [J]. TETRAHEDRON, 2008, 64 (22) : 5354 - 5361
  • [4] Areadi A., 1995, Synlett, P823
  • [5] Pd-catalyzed coupling reaction of acid chlorides with terminal alkynes using 1-(2-pyridylethynyl)-2-(2-thienylethynyl)benzene ligand
    Atobe, Shingo
    Masuno, Haruna
    Sonoda, Motohiro
    Suzuki, Yuki
    Shinohara, Hiroyuki
    Shibata, Satoshi
    Ogawa, Akiya
    [J]. TETRAHEDRON LETTERS, 2012, 53 (14) : 1764 - 1767
  • [6] Access to Flavones via a Microwave-Assisted, One-Pot Sonogashira-Carbonylation-Annulation Reaction
    Awuah, Emelia
    Capretta, Alfredo
    [J]. ORGANIC LETTERS, 2009, 11 (15) : 3210 - 3213
  • [7] Flexible Synthesis of Pyrimidines with Chiral Monofluorinated and Difluoromethyl Side Chains
    Bannwarth, Pierre
    Valleix, Alain
    Gree, Danielle
    Gree, Rene
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (12) : 4646 - 4649
  • [8] Palladium-catalyzed synthesis of aldehydes from aryl iodides and acetic formic anhydride
    Cacchi, S
    Fabrizi, G
    Goggiamani, A
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2004, 6 (05): : 692 - 694
  • [9] A remarkably efficient coupling of acid chlorides with alkynes in water
    Chen, L
    Li, CJ
    [J]. ORGANIC LETTERS, 2004, 6 (18) : 3151 - 3153
  • [10] Catalytic alkynone generation by Sonogashira reaction and its application in three-component pyrimidine synthesis
    D'Souza, Daniel M.
    Mueller, Thomas J. J.
    [J]. NATURE PROTOCOLS, 2008, 3 (10) : 1660 - 1665