CuI/PPh3/PEG-WATER: AN EFFICIENT CATALYTIC SYSTEM FOR CROSS-COUPLING REACTION OF ARYL IODIDES AND ALKYNES

被引:16
作者
Chen, Gong [1 ]
Xie, Jianwei [1 ]
Weng, Jiang [1 ]
Zhu, Xinhai [1 ]
Zheng, Zhanchao [1 ]
Cai, Jiwen [1 ]
Wan, Yiqian [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China
基金
国家高技术研究发展计划(863计划);
关键词
Alkynation; aqueous chemistry; copper; coupling; microwave-assisted chemistry; FREE SONOGASHIRA REACTION; COPPER-FREE; AMINE-FREE; LIGAND-FREE; POLY(ETHYLENE GLYCOL); TERMINAL ACETYLENES; PALLADIUM CATALYST; HALIDES; WATER; CARBON;
D O I
10.1080/00397911.2010.517363
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient protocol for the copper-catalyzed Sonogashira coupling of aryl iodides with terminal acetylenes in water-polyethylene glycol has been established. Both electron-rich and electron-deficient aryl iodides were arylalkynated under microwave heating or reflux in oil bath to afford good to excellent yields.
引用
收藏
页码:3123 / 3133
页数:11
相关论文
共 64 条
  • [1] Transition-metal-free Sonogashira-type coupling reactions in water
    Appukkuttan, P
    Dehaen, W
    Van der Eycken, E
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (24) : 4713 - 4716
  • [2] Pd/C-mediated coupling of aryl halides with terminal alkynes in water
    Batchu, VR
    Subramanian, V
    Parasuraman, K
    Swamy, NK
    Kumar, S
    Pal, M
    [J]. TETRAHEDRON, 2005, 61 (41) : 9869 - 9877
  • [3] Synthesis of 2-arylbenzo[b]furans via copper(I)-catalyzed coupling of o-iodophenols and aryl acetylenes
    Bates, CG
    Saejueng, P
    Murphy, JM
    Venkataraman, D
    [J]. ORGANIC LETTERS, 2002, 4 (26) : 4727 - 4729
  • [4] The nickel-catalyzed Sonogashira-Hagihara reaction
    Beletskaya, IP
    Latyshev, GV
    Tsvetkov, AV
    Lukashev, NV
    [J]. TETRAHEDRON LETTERS, 2003, 44 (27) : 5011 - 5013
  • [5] Palladium catalyzed alkynylation of aryl halides (Sonogashira reaction) in water
    Bhattacharya, S
    Sengupta, S
    [J]. TETRAHEDRON LETTERS, 2004, 45 (47) : 8733 - 8736
  • [6] Copper-free Sonogashira coupling reaction catalyzed by MCM-41-supported thioether palladium(0) complex in water under aerobic conditions
    Cai, Minzhong
    Xu, Qiuhua
    Sha, Junchao
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 272 (1-2) : 293 - 297
  • [7] Poly(ethylene glycol) (PEG) as a reusable solvent medium for organic synthesis. Application in the Heck reaction
    Chandrasekhar, S
    Narsihmulu, C
    Sultana, SS
    Reddy, NR
    [J]. ORGANIC LETTERS, 2002, 4 (25) : 4399 - 4401
  • [8] Pd/C-catalyzed cyanation of aryl halides in aqueous PEG
    Chen, Gong
    Weng, Jiang
    Zheng, Zhanchao
    Zhu, Xinhai
    Cai, Yaoyao
    Cai, Jiwen
    Wan, Yiqian
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (20) : 3524 - 3528
  • [9] Palladium-free copper-catalyzed coupling reaction of aryl iodides and terminal acetylenes in water
    Chen, Gong
    Zhu, Xinhai
    Cai, Jiwen
    Wan, Yiqian
    [J]. SYNTHETIC COMMUNICATIONS, 2007, 37 (7-9) : 1355 - 1361
  • [10] Polyethylene glycol and solutions of polyethylene glycol as green reaction media
    Chen, J
    Spear, SK
    Huddleston, JG
    Rogers, RD
    [J]. GREEN CHEMISTRY, 2005, 7 (02) : 64 - 82