An effective additive for copper-catalyzed hydroxylation of aryl iodides

被引:1
|
作者
Sakaguchi, Tomoya [1 ]
Shibata, Tomohiro [1 ]
Fukuda, Yusuke [1 ]
Tazawa, Aya [2 ]
Uozumi, Yasuhiro [2 ]
Matsumura, Yoshimasa [1 ]
Shimomura, Osamu [1 ]
Ohtaka, Atsushi [1 ]
机构
[1] Osaka Inst Technol, Fac Engn, Dept Appl Chem, 5-16-1 Ohmiya, Asahi, Osaka 5358585, Japan
[2] Inst Mol Sci IMS, Higashiyama 5-1, Myodaiji, Okazaki 4448787, Japan
基金
日本学术振兴会;
关键词
copper catalyst; hydroxylation; PEG; HIYAMA COUPLING REACTION; SUBSTITUTED CYCLOHEXANONES; PALLADIUM NANOPARTICLES; AEROBIC DEHYDROGENATION; RECYCLABLE CATALYST; EFFICIENT LIGAND; PHENOLS; HALIDES; ACID;
D O I
10.1002/aoc.7111
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Additive screening was conducted for copper-catalyzed hydroxylation of aryl iodides. Polyethylene glycol (PEG)-200 proved to be the most effective additive; whereas, longer chain PEGs (PEG-300, PEG-600, PEG-4000, and PEG-6000), other alcohols, and compounds including oxygen reduced the reaction efficiency. The reaction occurred smoothly under milder conditions than those reported previously. Using polystyrene-stabilized Cu nanoparticles as the catalyst, a reusable system could be established.
引用
收藏
页数:7
相关论文
共 50 条
  • [21] Copper-Catalyzed Hydroxylation of Aryl Halides Using Hydroxypicolinamide Ligands
    Widlicka, Daniel W.
    Singer, Robert A.
    Hotham, Ian
    Bernhardson, David J.
    Grosslight, Samantha
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2024, 28 (07) : 2732 - 2742
  • [22] Room-Temperature Practical Copper-Catalyzed Amination of Aryl Iodides
    Deldaele, Christopher
    Evano, Gwilherm
    CHEMCATCHEM, 2016, 8 (07) : 1319 - 1328
  • [23] Copper-Catalyzed Methylthiolation of Aryl Iodides and Bromides with Dimethyl Disulfide in Water
    Wang, Ying-yu
    Wu, Xiang-mei
    Yang, Ming-hua
    SYNLETT, 2020, 31 (12) : 1226 - 1230
  • [24] Copper-catalyzed cross-coupling of aryl acetylenes and vinyl iodides
    Venkataraman, D
    Bates, CG
    Saejueng, P
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U118 - U118
  • [25] Copper-catalyzed cross-coupling of diethyl phosphonate with aryl iodides
    Karlstedt, N. B.
    Beletskaya, I. P.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (07) : 1011 - 1014
  • [26] Copper-catalyzed amidation of aryl iodides in the presence of various chelating ligands
    Hosseinzadeh, Rahman
    Golchoubian, Hamid
    Masoudi, Mahtab
    JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2008, 55 (03) : 649 - 653
  • [27] Copper-catalyzed cross-coupling of diethyl phosphonate with aryl iodides
    N. B. Karlstedt
    I. P. Beletskaya
    Russian Journal of Organic Chemistry, 2011, 47 : 1011 - 1014
  • [28] COPPER-CATALYZED REACTION OF ARYL IODIDES WITH ACTIVE METHYLENE-COMPOUNDS
    OKURO, K
    FURUUNE, M
    MIURA, M
    NOMURA, M
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26): : 7606 - 7607
  • [29] Synthesis of N-aryl hydrazides by copper-catalyzed coupling of hydrazides with aryl iodides
    Wolter, M
    Klapars, A
    Buchwald, SL
    ORGANIC LETTERS, 2001, 3 (23) : 3803 - 3805
  • [30] Copper-catalyzed Hiyama coupling of aryl- and heteroaryltriethoxysilanes with aryl- and heteroaryl iodides
    Gurung, Santosh K.
    Thapa, Surendra
    Vangala, Adarsh S.
    Giri, Ramesh
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247