A Novel Protocol for the Cu-Catalyzed Sonogashira Coupling Reaction between Aryl Halides and Terminal Alkynes using trans-1,2-Diaminocyclohexane Ligand

被引:19
作者
Asha, Sujatha [1 ,2 ]
Thomas, Anns Maria [1 ,3 ]
Ujwaldev, Sankuviruthiyil M. [1 ]
Anilkumar, Gopinathan [1 ,4 ]
机构
[1] Mahatma Gandhi Univ, Sch Chem Sci, PD Hills PO, Kottayam 686560, Kerala, India
[2] Sree Vidyadhiraja NSS Coll, Vazhoor PO, Kottayam 686505, Kerala, India
[3] Nirmala Coll, Muvattupuzha PO, Ernakulam 686661, India
[4] Mahatma Gandhi Univ, Adv Mol Mat Res Ctr AMMRC, PD Hills PO, Kottayam 686560, Kerala, India
来源
CHEMISTRYSELECT | 2016年 / 1卷 / 13期
关键词
catalysis; copper; C-C coupling; Sonogashira coupling; 1,2-trans-diaminocyclohexane; PALLADIUM-FREE; DERIVATIVES; EFFICIENT; IODIDES; BENZOFURAN; ANALOGS; DABCO;
D O I
10.1002/slct.201600894
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient Sonogashira coupling reaction has been reported using cost effective and easily accessible CuI/trans-1,2-diaminocyclohexane catalytic system. The newly developed method can be successfully employed for the coupling between aryl and heteroaryl halides with terminal acetylenes. Furthermore this methodology can be extended for the one pot synthesis of biologically active benzofuran derivatives.
引用
收藏
页码:3938 / 3941
页数:4
相关论文
共 38 条
  • [1] Synthesis of cicerfuran, an antifungal benzofuran, and some related analogues
    Aslam, SN
    Stevenson, PC
    Phythian, SJ
    Veitch, NC
    Hall, DR
    [J]. TETRAHEDRON, 2006, 62 (17) : 4214 - 4226
  • [2] Poly(aryleneethynylene)s: Syntheses, properties, structures, and applications
    Bunz, UHF
    [J]. CHEMICAL REVIEWS, 2000, 100 (04) : 1605 - 1644
  • [3] On-water chemistry:: Copper-catalyzed straightforward synthesis of benzo[b]furan derivatives in neat water
    Carril, M
    SanMartin, R
    Tellitu, I
    Domínguez, E
    [J]. ORGANIC LETTERS, 2006, 8 (07) : 1467 - 1470
  • [4] Iron-catalyzed Sonogashira reactions
    Carril, Monica
    Correa, Arkaitz
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (26) : 4862 - 4865
  • [5] SYNTHESIS OF ARYL-SUBSTITUTED AND VINYL-SUBSTITUTED ACETYLENE DERIVATIVES BY USE OF NICKEL AND PALLADIUM COMPLEXES
    CASSAR, L
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) : 253 - 257
  • [6] Recent advances in Sonogashira reactions
    Chinchilla, Rafael
    Najera, Carmen
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 5084 - 5121
  • [7] Synthesis of potent agonists of the D-myo-inositol 1,4,5-trisphosphate receptor based on clustered disaccharide polyphosphate analogues of adenophostin A
    de Kort, M
    Correa, V
    Valentijn, ARPM
    van der Marel, GA
    Potter, BVL
    Taylor, CW
    van Boom, JH
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (17) : 3295 - 3303
  • [8] PALLADIUM CATALYZED SYNTHESIS OF ARYL, HETEROCYCLIC AND VINYLIC ACETYLENE DERIVATIVES
    DIECK, HA
    HECK, FR
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1975, 93 (02) : 259 - 263
  • [9] Diederich F., 1997, METAL CATALYZED CROS
  • [10] ERBER S, 1991, ANTI-CANCER DRUG DES, V6, P417