Copper-catalyzed synthesis of esters from ketones. Alkyl group as a leaving group

被引:12
|
作者
Nakatani, Yuji [1 ]
Koizumi, Yuichiro [1 ]
Yamasaki, Ryu [1 ]
Saito, Shinichi [1 ]
机构
[1] Tokyo Univ Sci, Fac Sci, Dept Chem, Tokyo 1628601, Japan
关键词
D O I
10.1021/ol800576w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The conversion of ketones to esters has been achieved through the use of Cu catalyst and tetrabutylammonium nitrite. This reaction involves the activation of the less activated C-C bond, and the alkyl group is removed as a leaving group. Various isopropyl ketones are found to be good substrates for this reaction.
引用
收藏
页码:2067 / 2070
页数:4
相关论文
共 50 条
  • [31] Copper-Catalyzed Cross-Coupling of Acylzirconocenes and Diaryliodonium Salts: An Efficient Synthesis of Alkyl-aryl-ketones from Alkenes
    Grosso, Simone
    Mlynczak, Marcelina
    Evano, Gwilherm
    Riant, Olivier
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (47)
  • [32] Ligand-Controlled Copper-Catalyzed Regiodivergent Carbonylative Synthesis of α-Amino Ketones and α-Boryl Amides from Imines and Alkyl Iodides
    Wu, Fu-Peng
    Wu, Xiao-Feng
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (02) : 695 - 700
  • [33] Triisopropylsilylhydrazine: A versatile protecting group for aldehydes and ketones.
    de Pomar, JCJ
    Santiago-Salinas, M
    Rivera-Sostre, D
    Soderquist, JA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U188 - U188
  • [34] MECHANISM OF COPPER-CATALYZED OXYGENATION OF KETONES
    SAYRE, LM
    JIN, SJ
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (19): : 3498 - 3503
  • [35] Copper-Catalyzed Coupling of Alkyl Vicinal Bis(boronic Esters) to an Array of Electrophiles
    Xu, Ningxin
    Kong, Ziyin
    Wang, Johnny Z.
    Lovinger, Gabriel J.
    Morken, James P.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (39) : 17815 - 17823
  • [36] Copper-catalyzed synthesis of arylcarboxamides from aldehydes and isocyanides: the isocyano group as an N1 synthon
    Liu, Jian-Quan
    Shen, Xuanyu
    Liu, Zhenhua
    Wang, Xiang-Shan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (30) : 6314 - 6317
  • [37] A NEW LEAVING GROUP IN ACETOLYSIS REACTIONS - SYNTHESIS OF ALKYL PICRATES
    SINNOTT, ML
    WHITING, MC
    CHEMICAL COMMUNICATIONS, 1968, (24) : 1617 - &
  • [38] Copper-Catalyzed Borylative Multicomponent Synthesis of Quaternary α-Amino Esters
    Yeung, Kay
    Talbot, Fabien J. T.
    Howell, Gareth P.
    Pulis, Alexander P.
    Procter, David J.
    ACS CATALYSIS, 2019, 9 (03) : 1655 - 1661
  • [39] Copper-catalyzed Decarboxylative Hydroboration: Synthesis of Vinyl Boronic Esters
    Irudayanathan, Francis Mariaraj
    Raja, Gabriel Charles Edwin
    Kim, Han-Sung
    Na, Kyungsu
    Lee, Sunwoo
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2016, 37 (04) : 463 - 468
  • [40] Copper-Catalyzed Aromatic Trifluoromethylation via Group Transfer from Fluoral Derivatives
    Kondo, Hideaki
    Oishi, Masahiro
    Fujikawa, Kenichi
    Amii, Hideki
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) : 1247 - 1252