Formation of 1,4-diketones by aerobic oxidative C-C coupling of styrene with 1,3-dicarbonyl compounds

被引：58
|
作者：
Rössle, M [1 ]
Werner, T [1 ]
Baro, A [1 ]
Frey, W [1 ]
Christoffers, J [1 ]
机构：
[1] Univ Stuttgart, Inst Organ Chem, D-70569 Stuttgart, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 47期
关键词：
dicarbonyl compounds; C-C coupling; cerium; heterocycles; homogeneous catalysis;
D O I：
10.1002/anie.200461406
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical equation presented). Convenient and direct: 1,4-Dicarbonyl compounds are readily obtained through a one-pot cerium-catalyzed oxidative C-C coupling in the presence of oxygen and subsequent fragmentation. The products are suitable precursors for heterocycles.
引用
收藏
页码：6547 / 6549
页数：3
相关论文
共 50 条
  • [1] Regiocontrolled Oxidative C-C Coupling of Dienol Ethers and 1,3-Dicarbonyl Compounds
    Liu, Xiaoguang
    Chen, Xiaohong
    Mohr, Justin T.
    ORGANIC LETTERS, 2016, 18 (13) : 3182 - 3185
  • [2] Copper/Iodine-Cocatalyzed C-C Cleavage of 1,3-Dicarbonyl Compounds Toward 1,2-Dicarbonyl Compounds
    Chen, Li-Sha
    Zhang, Lu-Bing
    Tian, Yue
    Li, Jin-Heng
    Liu, Yong-Quan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (34) : 5523 - 5526
  • [3] Lanthanide-Catalyzed Oxidative C-O Coupling of 1,3-Dicarbonyl Compounds with Diacyl Peroxides
    Terent'ev, Alexander O.
    Vil', Vera A.
    Nikishin, Gennady I.
    Adam, Waldemar
    SYNLETT, 2015, 26 (06) : 802 - 806
  • [4] Copper-catalyzed oxidative coupling of benzylic C-H bonds with 1,3-dicarbonyl compounds
    Borduas, Nadine
    Powell, David A.
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (19): : 7822 - 7825
  • [5] Palladium-Catalyzed C-C Bond Formation To Construct 1,4-Diketones under Mild Conditions
    Liu, Chao
    Deng, Yi
    Wang, Jing
    Yang, Yingying
    Tang, Shan
    Lei, Aiwen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (32) : 7337 - 7341
  • [6] Construction of quaternary alkyl motifs through palladium-catalyzed oxidative coupling of 1,3-dicarbonyl compounds with alkenes followed by C-C bond cleavage
    Zhang, Xu
    Chang, Mengfan
    Ni, Tongtong
    Xu, Xuefeng
    Zong, Luyi
    Li, Ting
    CHEMICAL COMMUNICATIONS, 2024, 60 (78) : 10958 - 10961
  • [7] SELECTIVE C-ALKYLATION OF 1,3-DICARBONYL COMPOUNDS
    ANTONIOLETTI, R
    BONADIES, F
    ORELLI, LR
    SCETTRI, A
    GAZZETTA CHIMICA ITALIANA, 1992, 122 (06): : 237 - 238
  • [8] Electrochemical Radical Reaction Construction of C-C Bonds: Access to 1,4-Dicarbonyl Compounds from Enol Acetates and 1,3-Diketones
    Wu, Fan
    Liu, Shengjun
    Lv, Xiaoqing
    Pan, Mei
    Liu, Xiaoqin
    Zhang, Jinpeng
    Rong, Liangce
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (19): : 13749 - 13759
  • [9] Oxidative Coupling of 1,3-Dicarbonyl Compounds by Cerium(IV) Ammonium Nitrate
    Song, Jianan
    Zhang, Hao
    Chen, Xianjun
    Li, Xinsheng
    Xu, Dongcheng
    SYNTHETIC COMMUNICATIONS, 2010, 40 (12) : 1847 - 1855
  • [10] Facile synthesis of 1,4-diketones via three-component reactions of α-ketoaldehyde, 1,3-dicarbonyl compound, and a nucleophile in water
    Yang, Jian
    Mei, Fuming
    Fu, Shitao
    Gu, Yanlong
    GREEN CHEMISTRY, 2018, 20 (06) : 1367 - 1374
12345