Synthesis of Benzoxazole and Benzimidazole Derivatives via Ligand-Free Copper(I)-Catalyzed Cross-Coupling Reaction of o-Halophenols or o-Haloanilines with Carbodiimides

被引:57
|
作者
Shen, Guodong [1 ]
Bao, Weiliang [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China
关键词
copper(I) catalysis; cross-coupling; heterocycles; ligand-free conditions; one-pot reaction; STREPTOMYCES SP 517-02; STRUCTURE-BASED DESIGN; N BOND FORMATION; C-N; EFFICIENT SYNTHESIS; CYTOTOXIC METABOLITE; CATALYZED SYNTHESIS; COPPER; ARYLATION; NITROGEN;
D O I
10.1002/adsc.201000022
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A novel and efficient synthesis of benzoxazole and benzimidazole derivatives via a ligand-free, copper(I)-catalyzed, one-pot cascade process has been developed. A variety of carbodiimides coupled with o-halophenols or o-haloanilines to give the products in moderate to excellent yields under the mild conditions.
引用
收藏
页码:981 / 986
页数:6
相关论文
共 50 条
  • [21] Ligand-free copper(I) catalyzed N- and O-arylation of aryl halides
    Sperotto, Elena
    de Vries, Johannes G.
    van Klink, Gerard P. M.
    van Koten, Gerard
    TETRAHEDRON LETTERS, 2007, 48 (41) : 7366 - 7370
  • [22] Sustainable Ligand-Free Heterogeneous Palladium-Catalyzed Sonogashira Cross-Coupling Reaction in Deep Eutectic Solvents
    Messa, Francesco
    Dilauro, Giuseppe
    Perna, Filippo M.
    Vitale, Paola
    Capriati, Vito
    Salomone, Antonio
    CHEMCATCHEM, 2020, 12 (07) : 1979 - 1984
  • [23] Copper catalyzed C-O bond formation via oxidative cross-coupling reaction of aldehydes and ethers
    Wang, Quan
    Zheng, Hao
    Chai, Wen
    Chen, Dianyu
    Zeng, Xiaojun
    Fu, Renzhong
    Yuan, Rongxin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (34) : 6549 - 6553
  • [24] TBAB-promoted ligand-free copper-catalyzed cross-coupling reactions of aryl halides with arylboronic acids
    Li, Jin-Heng
    Li, Ji-Lan
    Xie, Ye-Xiang
    SYNTHESIS-STUTTGART, 2007, (07): : 984 - 988
  • [25] Pd0.02Ce0.98O2-δ: a copper- and ligand-free quasi-heterogeneous catalyst for aquacatalytic Sonogashira cross-coupling reaction
    Mpungose, P. P.
    Sehloko, N. I.
    Cwele, T.
    Maguire, G. E. M.
    Friedrich, H. B.
    JOURNAL OF THE SOUTHERN AFRICAN INSTITUTE OF MINING AND METALLURGY, 2017, 117 (10) : 955 - 962
  • [26] Pd/C-Catalyzed Ligand-Free Hiyama Cross-Coupling Reaction of Aryl Halides Under Aqueous Conditions
    Mittapelly, Nagaraju
    Mukkanti, Khagga
    Reguri, Buchi Reddy
    ASIAN JOURNAL OF CHEMISTRY, 2014, 26 (04) : 1015 - 1018
  • [27] Efficient ligand-free Hiyama cross-coupling reaction catalyzed by functionalized SBA-15-supported Pd nanoparticles
    Huang, Shao-Hsien
    Liu, Chun-Hsia
    Yang, Chia-Min
    GREEN CHEMISTRY, 2014, 16 (05) : 2706 - 2712
  • [28] Copper- and Ligand-Free Sonogashira Cross-Coupling: Access to Novel 3-Aminoindole Derivatives and Their Biological Evaluations
    Rikhotso, Tshikani D.
    Poopedi, Kgomotso W.
    Nxumalo, Winston
    Leboho, Tlabo C.
    JOURNAL OF CHEMISTRY, 2023, 2023
  • [29] Synthesis of arylboronates via the palladium(O)-catalyzed cross-coupling reaction of tetra(alkoxo)diborons with aryl triflates
    Ishiyama, T
    Itoh, Y
    Kitano, T
    Miyaura, N
    TETRAHEDRON LETTERS, 1997, 38 (19) : 3447 - 3450
  • [30] Ligand-free Pd/C-catalyzed Suzuki-Miyaura coupling reaction for the synthesis of heterobiaryl derivatives
    Kitamura, Yoshiaki
    Sako, Satoko
    Udzu, Takahiro
    Tsutsui, Azusa
    Maegawa, Tomohiro
    Monguchi, Yasunari
    Sajiki, Hironao
    CHEMICAL COMMUNICATIONS, 2007, (47) : 5069 - 5071