Oxidative dimerization of primary alcohols to esters catalyzed by iridium complexes

被引:54
|
作者
Izumi, Aki
Obora, Yasushi
Sakaguchi, Satoshi
Ishii, Yasutaka [1 ]
机构
[1] Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
[2] Kansai Univ, Fac Engn, High Technol Res Ctr, Suita, Osaka 5648680, Japan
关键词
iridium; primary alcohol; ester;
D O I
10.1016/j.tetlet.2006.10.144
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Primary alcohols undergo efficiently oxidative dimerization by iridium complexes under air without any solvent to form esters in fair to good yields. For instance, the reaction of 1-dodecanol in the presence of [IrCI(coe)(2)](2) (3 mol %) at 95 degrees C for 15 h produced dodecyl dodecanoate in 91% isolated yield. This is the first successful Ir-catalyzed oxidative dimerization of primary alcohols to esters using air as an oxidant. Various primary alcohols are converted to the corresponding esters in fair to good yields. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9199 / 9201
页数:3
相关论文
共 50 条
  • [41] Mechanistic Investigations of the Iridium(III)-Catalyzed Aerobic Oxidation of Primary and Secondary Alcohols
    Jiang, Bi
    Feng, Yuee
    Ison, Elon A.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (44) : 14462 - +
  • [42] Tuning the selectivity in iridium-catalyzed acceptorless dehydrogenative coupling of primary alcohols
    Tabasi, Nihal S.
    Genc, Sertac
    Gulcemal, Derya
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (33) : 6582 - 6592
  • [43] Mechanistic investigations of the iridium(III) catalyzed aerobic oxidation of primary and secondary alcohols
    Ison, Elon A.
    Jiang, Bi
    Feng, Yuee
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
  • [44] Computational mechanistic study on oxidative esterification of alcohols to esters catalyzed by palladium complex
    Hu, Wei
    Li, Jing
    Deng, Suwen
    Huang, Jianyin
    Le, Xueyi
    Zheng, Wenxu
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 740 : 10 - 16
  • [45] Clean preparation of methyl esters in one-step oxidative esterification of primary alcohols catalyzed by supported gold nanoparticles
    Oliveira, Rafael L.
    Kiyohara, Pedro K.
    Rossi, Liane M.
    GREEN CHEMISTRY, 2009, 11 (09) : 1366 - 1370
  • [46] REDUCED COPPER-CATALYZED CONVERSION OF A MIXTURE OF PRIMARY ALCOHOLS AND SECONDARY ALCOHOLS INTO ESTERS AND KETONES
    TAKESHITA, K
    KAWAMOTO, K
    SUGA, T
    NIPPON KAGAKU KAISHI, 1988, (10) : 1698 - 1703
  • [47] Experimental and Theoretical Mechanistic Investigation of the Iridium-Catalyzed Dehydrogenative Decarbonylation of Primary Alcohols
    Olsen, Esben P. K.
    Singh, Thishana
    Harris, Pernille
    Andersson, Pher G.
    Madsen, Robert
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (02) : 834 - 842
  • [48] Structure-Activity Relationship in the Iridium-Catalyzed Isomerization of Primary Allylic Alcohols
    Mantilli, Luca
    Gerard, David
    Besnard, Celine
    Mazet, Clement
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2012, (20) : 3320 - 3330
  • [49] Iridium-Pyrazolato Complex Catalyzed Dehydrogenative Alkylation of Ketones and Arylacetonitriles with Primary Alcohols
    Panda, Surajit
    Maharana, Suraj Kumar
    Saha, Ratnakar
    Bagh, Bidraha
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024,
  • [50] Iridium-catalyzed isomerization of primary allylic alcohols under mild reaction conditions
    Mantilli, Luca
    Mazet, Clement
    TETRAHEDRON LETTERS, 2009, 50 (28) : 4141 - 4144