Study of the microwave-assisted hydrolysis of nitriles and esters and the implementation of this system in rapid microwave-assisted Pd-catalyzed amination

被引:46
|
作者
Van Baelen, Gitte [1 ]
Maes, Bert U. W. [1 ]
机构
[1] Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium
关键词
hydrolysis; nitrile; ester; phase transfer catalyst; two phase system; microwave irradiation; Buchwald-Hartwig reaction; aryl chlorides; heterocycles;
D O I
10.1016/j.tet.2008.03.028
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Microwave-assisted hydrolysis of benzonitriles and methyl benzoates has been studied using a toluene/concd aq KOH two phase system in the presence and absence of phase transfer catalyst. Conditions to allow and avoid smooth hydrolysis could be identified. Based on the latter, the first microwave protocol which allows the rapid Pd-catalyzed amination of aliphatic amines with chlorobenzenes containing sensitive functional groups has been developed. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5604 / 5619
页数:16
相关论文
共 50 条
  • [21] Microwave-assisted Pd-catalyzed cross-coupling of aryl alkyl selenides with arylboronic acids
    Sapra, Shivani
    Kumar, Sumit
    Singh, Brajendra K.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (11) : 2590 - 2596
  • [22] Microwave-assisted catalytic synthesis of phytosterol esters
    Zhang, Yaru
    Zhang, Tao
    Zhang, Yu
    Wu, Zhengzhang
    Zhang, Peng
    Liu, Ruijie
    Chang, Ming
    Wang, Xingguo
    INTERNATIONAL JOURNAL OF FOOD SCIENCE AND TECHNOLOGY, 2022, 57 (05): : 3162 - 3170
  • [23] Microwave-assisted Weak Acid Hydrolysis of Proteins
    Seo, Miyeong
    Kim, Jinhee
    Park, Sehwan
    Lee, Ji-Hye
    Kim, Taehee
    Lee, Jihyeon
    Kim, Jeongkwon
    MASS SPECTROMETRY LETTERS, 2012, 3 (02) : 47 - 49
  • [24] Microwave-assisted transformation of esters into hydroxamic acids
    Massaro, Assunta
    Mordini, Alessandro
    Reginato, Gianna
    Russo, Francesco
    Taddei, Maurizio
    SYNTHESIS-STUTTGART, 2007, 20 (20): : 3201 - 3204
  • [25] Microwave-assisted preparation of naphthenic acid esters
    Cirin-Novta, Vera
    Kuhajda, Ksenija
    Kevresan, Slavko
    Kandrac, Julijan
    Grbovic, Ljubica
    Vujic, Djura
    JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 2006, 71 (12) : 1263 - 1268
  • [26] Microwave-assisted preparation of aryltetrazoleboronate esters.
    Schulz, MJ
    Coats, SJ
    Hlasta, DJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U149 - U149
  • [27] Microwave-Assisted Regiospecific Synthesis of Pseudohalohydrin Esters
    El Khatib, Mirna
    Elagawany, Mohamed
    Todadze, Ekaterina
    Khelashvili, Levan
    El-Feky, Said A.
    Katritzky, Alan R.
    SYNLETT, 2012, (09) : 1384 - 1388
  • [28] A Complete Degradation of Organophosphates by Microwave-Assisted Hydrolysis
    Jansa, Petr
    Cechova, Lucie
    Janeba, Zlatko
    CURRENT MICROWAVE CHEMISTRY, 2016, 3 (03) : 219 - 226
  • [29] A convenient microwave-assisted 5-amination of flavones
    Lecoutey, Cedric
    Fossey, Christine
    Demuynck, Luc
    Lefoulon, Francois
    Fabis, Frederic
    Rault, Sylvain
    TETRAHEDRON, 2008, 64 (49) : 11243 - 11248
  • [30] Microwave-assisted conversion of oximes into nitriles in the presence of a zeolite
    Hegedüs, A
    Cwik, A
    Hell, Z
    Horváth, Z
    Esek, A
    Uzsoki, M
    GREEN CHEMISTRY, 2002, 4 (06) : 618 - 620