Copper-Catalyzed C-O Bond Formation: An Efficient One-Pot Highly Regioselective Synthesis of Furans from (2-Furyl)Carbene Complexes

被引:124
作者
Cao, Hua [1 ]
Zhan, Haiying [1 ]
Cen, Jinghe [1 ]
Lin, Jingxin [1 ]
Lin, Yuanguang [1 ]
Zhu, Qiuxia [1 ]
Fu, Minling [1 ]
Jiang, Huanfeng [2 ]
机构
[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou 510006, Guangdong, Peoples R China
[2] S China Univ Technol, Sch Chem & Chem Engn, Guangzhou 510640, Guangdong, Peoples R China
关键词
FISCHER CARBENE COMPLEXES; ELECTRON-DEFICIENT ALKYNES; 2,3-ALLENOIC ACIDS; DOMINO PROCESS; 2,5-DISUBSTITUTED FURANS; POLYSUBSTITUTED FURANS; BIOLOGICAL EVALUATION; CYCLIZATION REACTION; KETONES; DERIVATIVES;
D O I
10.1021/ol400080e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient one-pot Cu(I)-catalyzed strategy for regioselective synthesis of trisubstituted furan derivatives has been developed via (2-furyl) carbene complexes. This process has opened a new synthetic route to a variety of alpha-carbonyl furans using air as the oxidant affording furans in good yields.
引用
收藏
页码:1080 / 1083
页数:4
相关论文
共 55 条
  • [1] [Anonymous], 2009, ANGEW CHEM
  • [2] Metal-controlled selective [3+2] cyclization reactions of alkenyl Fischer carbene complexes and allenes
    Barluenga, J
    Vicente, R
    Barrio, P
    López, LA
    Tomás, M
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (19) : 5974 - 5975
  • [3] [3+2] cycloaddition of Fischer alkenyl carbene complexes to enamines:: An efficient asymmetric approach to cyclopentanoids
    Barluenga, J
    Tomás, M
    Ballesteros, A
    Santamaría, J
    Brillet, C
    García-Granda, S
    Piñera-Nicolás, A
    Vázquez, JT
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (18) : 4516 - 4517
  • [4] Cu(I)-catalyzed regioselective synthesis of polysubstituted furans from propargylic esters via postulated (2-furyl)carbene complexes
    Barluenga, Jose
    Riesgo, Lorena
    Vicente, Ruben
    Lopez, Luis A.
    Tomas, Miguel
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (41) : 13528 - +
  • [5] A general and regioselective synthesis of cyclopentenone derivatives through nickel(0)-mediated [3+2] cyclization of alkenyl Fischer carbene complexes and internal alkynes
    Barluenga, Jose
    Barrio, Pablo
    Riesgo, Lorena
    Lopez, Luis. A.
    Tomas, Miguel
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (46) : 14422 - 14426
  • [6] Enantioselective Carbonyl Allylation, Crotylation, and tert-Prenylation of Furan Methanols and Furfurals via Iridium-Catalyzed Transfer Hydrogenation
    Bechem, Benjamin
    Patman, Ryan L.
    Hashmi, A. Stephen K.
    Krische, Michael J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) : 1795 - 1798
  • [7] N-Heterocyclic Carbene-Catalyzed Cascade Reaction Involving the Hydroacylation of Unactivated Alkynes
    Biju, Akkattu T.
    Wurz, Nathalie E.
    Glorius, Frank
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (17) : 5970 - +
  • [8] Design, synthesis, and biological activity of prazosin-related antagonists.: Role of the piperazine and furan units of prazosin on the selectivity for α1-adrenoreceptor subtypes
    Bolognesi, ML
    Budriesi, R
    Chiarini, A
    Poggesi, E
    Leonardi, A
    Melchiorre, C
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (24) : 4844 - 4853
  • [9] Cao H., 2011, ORG BIOMOL CHEM, V21, P7257
  • [10] Transition-Metal-Catalyzed Domino Reactions: Efficient One-Pot Regiospecific Synthesis of Highly Functionalized Polysubstituted Furans from Electron-Deficient Alkynes and 2-Yn-1-ols
    Cao, Hua
    Jiang, Huanfeng
    Huang, Huawen
    [J]. SYNTHESIS-STUTTGART, 2011, (07): : 1019 - 1036