Highly efficient Pd-catalyzed synthesis of nitriles from aldoximes

被引:76
|
作者
Kim, Hoo Sook
Kim, Sung Hwan
Kim, Jae Nyoung [1 ]
机构
[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea
关键词
Palladium; Nitriles; Aldoximes; ALLYLATED OXIME ETHERS; HECK-TYPE CYCLIZATION; C-H BONDS; HETEROGENEOUS CATALYST; ALLYLIC SUBSTITUTION; AROMATIC NITRILES; PRIMARY AMIDES; ARYL HALIDES; DEHYDRATION; OXYGENATION;
D O I
10.1016/j.tetlet.2009.01.150
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An expedient method of Pd-catalyzed conversion of aldoxime into nitrile was developed. The reaction was carried out under the influence of Pd(OAc)(2)/PPh3 in refluxing CH3CN to provide good to high yields. The use of Cs2CO3 (0.1-0.5 equiv) was crucial in some cases. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1717 / 1719
页数:3
相关论文
共 50 条
  • [1] EFFICIENT SYNTHESIS OF NITRILES FROM ALDOXIMES
    HENDRICKSON, JB
    BAIR, KW
    KEEHN, PM
    [J]. TETRAHEDRON LETTERS, 1976, (08) : 603 - 604
  • [2] Cobalt(II) catalyzed dehydration of aldoximes: A highly efficient practical procedure for the synthesis of nitriles
    Tamilselvan, Pitchiah
    Basavaraju, Yeriyur B.
    Sampathikumar, Ellappan
    Murugesan, Ramachandran
    [J]. CATALYSIS COMMUNICATIONS, 2009, 10 (05) : 716 - 719
  • [3] Highly efficient and catalytic conversion of aldoximes to nitriles
    Yang, SH
    Chang, SB
    [J]. ORGANIC LETTERS, 2001, 3 (26) : 4209 - 4211
  • [4] Pd-catalyzed synthesis of highly functionalized piperidines
    Allen, Benjamin
    Harrity, Joseph
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [5] A NOVEL SYNTHESIS OF NITRILES FROM ALDOXIMES
    MORALES, J
    ORTIZ, M
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 207 : 330 - CHED
  • [6] Efficient synthesis of akolactone a via Pd-catalyzed carbonylation
    Makabe, H
    Okajima, M
    Konno, H
    Kan, T
    Hirota, M
    [J]. BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2003, 67 (12) : 2658 - 2660
  • [7] A Simple Synthesis of Nitriles from Aldoximes
    Singh, Manish K.
    Lakshman, Mahesh K.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (08): : 3079 - 3084
  • [8] Total synthesis of enantiopure (+)-γ-lycorane using highly efficient Pd-catalyzed asymmetric allylic alkylation
    Chapsal, BD
    Ojima, I
    [J]. ORGANIC LETTERS, 2006, 8 (07) : 1395 - 1398
  • [9] Highly Enantioselective Synthesis of Sultams via Pd-Catalyzed Hydrogenation
    Yu, Chang-Bin
    Wang, Da-Wei
    Zhou, Yong-Gui
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15): : 5633 - 5635
  • [10] Pd-Catalyzed α-Arylation of Nitriles and Esters and γ-Arylation of Unsaturated Nitriles with TMPZnCl•LiCl
    Duez, Stephanie
    Bernhardt, Sebastian
    Heppekausen, Johannes
    Fleming, Fraser F.
    Knocher, Paul
    [J]. ORGANIC LETTERS, 2011, 13 (07) : 1690 - 1693