Transition-metal-free oxidative amidation of benzyl alcohols with amines catalyzed by NaI: a new method for the synthesis of benzamides

被引:30
作者
Karimi, Meghdad [1 ]
Saberi, Dariush [2 ]
Azizi, Kobra [1 ]
Arefi, Marzban [1 ]
Heydari, Akbar [1 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, Tehran, Iran
[2] Persian Gulf Univ, Coll Agr & Nat Resources, Dept Fisheries & Aquaculture, Bushehr 75169, Iran
关键词
Benzyl alcohol; Amine; Oxidative amidation; Sodium iodide; AMIDE BOND FORMATION; CARBOXYLIC-ACIDS; TERTIARY-AMINES; MILD AMIDATION; ALDEHYDES; HYDROCHLORIDE; TRANSAMIDATION; AMINATION; SECONDARY; PEPTIDES;
D O I
10.1016/j.tetlet.2014.07.085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, inexpensive, and efficient method for the synthesis of benzamides via the reaction of benzyl alcohols and amine hydrochloride salts in the presence of NaI as a green catalyst is described. Various derivatives of benzamide were synthesized in moderate to good yields using this method. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5351 / 5353
页数:3
相关论文
共 69 条
  • [1] Transamidation of Primary Amides with Amines Using Hydroxylamine Hydrochloride as an Inorganic Catalyst
    Allen, C. Liana
    Atkinson, Benjamin N.
    Williams, Jonathan M. J.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (06) : 1383 - 1386
  • [2] Direct amide formation from unactivated carboxylic acids and amines
    Allen, C. Liana
    Chhatwal, A. Rosie
    Williams, Jonathan M. J.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (05) : 666 - 668
  • [3] Copper-Catalyzed Direct Synthesis of Benzamides from Alcohols and Amines
    Bantreil, Xavier
    Fleith, Clement
    Martinez, Jean
    Lamaty, Frederic
    [J]. CHEMCATCHEM, 2012, 4 (12) : 1922 - 1925
  • [4] N-heterocyclic carbene-catalyzed redox amidations of α-functionalized aldehydes with amines
    Bode, Jeffrey W.
    Sohn, Stephanie S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (45) : 13798 - +
  • [5] Palladium-Catalyzed Carbonylation Reactions of Aryl Halides and Related Compounds
    Brennfuehrer, Anne
    Neumann, Helfried
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (23) : 4114 - 4133
  • [6] Oxidative amide synthesis and N-terminal α-amino group ligation of peptides in aqueous medium
    Chan, Wing-Kei
    Ho, Chi-Ming
    Wong, Man-Kin
    Che, Chi-Ming
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (46) : 14796 - 14797
  • [7] Practical synthesis of amides from alkynyl bromides, amines, and water
    Chen, Zheng-Wang
    Jiang, Huan-Feng
    Pan, Xiao-Yan
    He, Zai-Jun
    [J]. TETRAHEDRON, 2011, 67 (33) : 5920 - 5927
  • [8] Copper-catalyzed hydrative amide synthesis with terminal alkyne, sulfonyl azide, and water
    Cho, SH
    Yoo, EJ
    Bae, L
    Chang, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (46) : 16046 - 16047
  • [9] Acylation of amines with carboxylic acids: the atom economic protocol catalysed by Fe(III)-montmorillonite
    Choudary, BM
    Bhaskar, V
    Kantam, ML
    Rao, KK
    Raghavan, K
    [J]. CATALYSIS LETTERS, 2001, 74 (3-4) : 207 - 211
  • [10] Atmospheric pressure aminocarbonylation of aryl iodides using palladium nanoparticles supported on MOF-5
    Dang, Tuan T.
    Zhu, Yinghuai
    Ghosh, Subhash C.
    Chen, Anqi
    Chai, Christina L. L.
    Seayad, Abdul M.
    [J]. CHEMICAL COMMUNICATIONS, 2012, 48 (12) : 1805 - 1807