Nickel(0)-Catalyzed N-Allylation of Amides and p-Toluenesulfonamide with Allylic Alcohols under Neat and Neutral Conditions

被引:29
|
作者
Azizi, Mohamed Salah [1 ]
Edder, Youssef [2 ]
Karim, Abdallah [2 ]
Sauthier, Mathieu [1 ]
机构
[1] Univ Artois, ENSCL, Cent Lille, Univ Lille,CNRS,UMR 8181,UCCS, F-59000 Lille, France
[2] Univ Cadi Ayyad, Equipe Chim Coordinat & Catalyse, Dept Chim, Fac Sci Semlalia, BP 2390, Marrakech, Morocco
关键词
Homogeneous catalysis; Nickel; N-Allylation; Allylic alcohols; Amides; Electron-poor N atoms; CATALYZED HYDROALKOXYLATION REACTION; ONE-POT SYNTHESIS; ALLYLAMINE DERIVATIVES; CLAISEN REARRANGEMENT; 3-COMPONENT REACTION; DIRECT SUBSTITUTION; HYDROXY GROUP; COMPLEXES; PALLADIUM; NUCLEOPHILES;
D O I
10.1002/ejoc.201600500
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nickel(0)-catalyzed direct N-allylation of amides and p-toluenesulfonamide with allylic alcohols took place in the presence of Ni-0-diphosphine complexes. The corresponding N-allylated (and/or N, N-diallylated) products were obtained in moderate to high yields under neutral conditions.
引用
收藏
页码:3796 / 3803
页数:8
相关论文
共 21 条
  • [1] Amide Acetal in Palladium-Catalyzed Allylation with Allylic Alcohols under Neutral Conditions
    Kwon, Yongseok
    Jung, Jaehyun
    Kim, Jae Hyun
    Kim, Woo-Jung
    Kim, Sanghee
    [J]. ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 6 (05) : 520 - 526
  • [2] An efficient FeCl3-catalyzed amidation reaction of secondary benzylic and allylic alcohols with carboxamides or p-toluenesulfonamide
    Jana, Umasish
    Maiti, Sukhendu
    Biswas, Srijit
    [J]. TETRAHEDRON LETTERS, 2008, 49 (05) : 858 - 862
  • [3] Neutral nickel-catalyzed dehydrosulfonylation of unactivated allylic alcohols under mild conditions
    Yang, Yahui
    Zhu, Haibo
    Gong, Bozhen
    Yang, Hong
    Fan, Qiangwen
    Le, Zhang-Gao
    Xie, Zongbo
    [J]. CHEMICAL COMMUNICATIONS, 2024, 60 (18) : 2516 - 2519
  • [4] A substrate-dependent mechanism for nickel-catalyzed N-allylation with allylic alcohols: nucleophilic attack vs. reductive elimination
    Yao, Ruiming
    Jing, Yaru
    Liu, Jiahao
    Liu, Yan
    Wang, Tiejun
    Ke, Zhuofeng
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (11) : 2721 - 2727
  • [5] Palladium-catalyzed C-allylation of naphthols by direct use of allylic alcohols under neutral conditions
    Tada, Y
    Satake, A
    Shimizu, I
    Yamamoto, A
    [J]. CHEMISTRY LETTERS, 1996, (12) : 1021 - 1022
  • [6] B(C6F5)3-Catalyzed N-Allylation of Hydrazines with Allylic Alcohols
    Xu, Boxia
    Yang, Ji
    Yao, Zhen
    Yang, Zhuo
    Liu, Kai
    Jin, Xing
    Xu, Lijin
    Shi, Qian
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (05) : 1176 - 1181
  • [7] The Selective Nickel-Catalyzed N-Allylation of C3-Unprotected Indoles under Mild and Clean Conditions
    Mouhsine, Bouchaib
    Karim, Abdallah
    Dumont, Clement
    Saint Pol, Anthony
    Suisse, Isabelle
    Sauthier, Mathieu
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (26)
  • [8] Silylation of Alcohols and Phenols Using Hexamethyldisilazane Catalyzed by N,N'-Diiodo-N,N'-1,2-ethanediyl Bis(p-toluenesulfonamide) Under Solvent-Free and Microwave Conditions
    Ghorbani-Vaghei, Ramin
    Malaekehpoor, Seyedeh Mina
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2010, 185 (03) : 582 - 587
  • [9] PALLADIUM AND ARSENIC(III) OXIDE-CATALYZED ALLYLIC ALKYLATION BY ALLYLIC ALCOHOLS UNDER NEUTRAL CONDITIONS
    LU, XY
    LU, L
    SUN, JH
    [J]. JOURNAL OF MOLECULAR CATALYSIS, 1987, 41 (1-2): : 245 - 251
  • [10] Nickel-Catalyzed Chemoselective Acetalization of Aldehydes With Alcohols under Neutral Conditions
    Subaramanian, Murugan
    Landge, Vinod G.
    Mondal, Akash
    Gupta, Virendrakumar
    Balaraman, Ekambaram
    [J]. CHEMISTRY-AN ASIAN JOURNAL, 2019, 14 (24) : 4557 - 4562