Synthesis of enol and vinyl esters catalyzed by an iridium complex

被引:68
|
作者
Nakagawa, H [1 ]
Okimoto, Y [1 ]
Sakaguchi, S [1 ]
Ishii, Y [1 ]
机构
[1] Kansai Univ, Fac Engn, Dept Appl Chem, Suita, Osaka 5648680, Japan
关键词
iridium; enol ether; vinyl ether; alkyne; carboxylic acid; vinyl acetate;
D O I
10.1016/S0040-4039(02)02451-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Enol and vinyl esters were successfully synthesized by the use of an iridium complex as a catalyst. The reaction of carboxylic acid with terminal alkynes in the presence of catalytic amounts of [Ir(cod)Cl](2) and Na2CO3 gave the corresponding I-alkenyl esters. The addition of carboxylic acids to alkynes principally took place in the Markovnikov fashion. In addition, by the use of an Ir complex combined with NaOAc various vinyl esters were prepared through the transvinylation between carboxylic acids and vinyl acetate. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:103 / 106
页数:4
相关论文
共 50 条
  • [21] RUTHENIUM COMPLEX CATALYZED SELECTIVE ADDITION OF CARBOXYLIC-ACIDS TO ACETYLENES GIVING ENOL ESTERS
    MITSUDO, T
    HORI, Y
    YAMAKAWA, Y
    WATANABE, Y
    [J]. TETRAHEDRON LETTERS, 1986, 27 (19) : 2125 - 2126
  • [22] Asymmetric epoxidation of (Z)-enol esters catalyzed by titanium(salalen) complex with aqueous hydrogen peroxide
    Matsumoto, Kazuhiro
    Feng, Chao
    Handa, Satoshi
    Oguma, Takuya
    Katsuki, Tsutomu
    [J]. TETRAHEDRON, 2011, 67 (35) : 6474 - 6478
  • [23] Synthesis of alpha-arylthioalkyl esters: The addition reactions of vinyl esters with arylthiols catalyzed by lipase
    Lee, RS
    [J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1997, 44 (01) : 77 - 80
  • [24] Iridium-Catalyzed Reductive Allylation of Esters
    Xie, Lan-Gui
    Rogers, Jack
    Anastasiou, Ioannis
    Leitch, Jamie A.
    Dixon, Darren J.
    [J]. ORGANIC LETTERS, 2019, 21 (17) : 6663 - 6667
  • [25] Stereoselective synthesis of silyl enol ethers via the iridium-catalyzed isomerization of allyl silyl ethers
    Ohmura, T
    Yamamoto, Y
    Miyaura, N
    [J]. ORGANOMETALLICS, 1999, 18 (03) : 413 - 416
  • [26] Stereoselective synthesis of (E)-α,β-unsaturated esters: triethylamine-catalyzed allylic rearrangement of enol phosphates
    Zhang, Yulong
    Guo, Huichuang
    Wu, Qian
    Bi, Xiaojing
    Shi, Enxue
    Xiao, Junhua
    [J]. RSC ADVANCES, 2023, 13 (20) : 13511 - 13515
  • [27] Synthesis of enol esters and dimerization of terminal alkynes catalyzed by neutral and cationic vinylidene ruthenium complexes
    Opstal, T
    Verpoort, F
    [J]. SYNLETT, 2003, (03) : 314 - 320
  • [28] Rh-Catalyzed Asymmetric Hydrogenation of β-Branched Enol Esters for the Synthesis of β-Chiral Primary Alcohols
    Liu, Chong
    Yuan, Jing
    Zhang, Jian
    Wang, Zhihui
    Zhang, Zhenfeng
    Zhang, Wanbin
    [J]. ORGANIC LETTERS, 2018, 20 (01) : 108 - 111
  • [29] Rhodium-Catalyzed Reaction of Diazonaphthoquinones and Enol Ethers: Synthesis of Dihydronaphthofuran Derivatives and α-Naphthyl Esters
    Kitamura, Mitsuru
    Araki, Keiichiro
    Matsuzaki, Hiroki
    Okauchi, Tatsuo
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (23) : 5045 - 5049
  • [30] PALLADIUM-CATALYZED ARYLATION OF 4-CHROMANONE ENOL ESTERS - NEW SYNTHESIS OF ISOFLAVANONES
    SAITO, R
    IZUMI, T
    KASAHARA, A
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1973, 46 (06) : 1776 - 1779