The Heck reaction of polymer-supported allylamine with aryl iodides

被引：7
|
作者：
Leikoski, Tuomo [1 ]
Wrigstedt, Pauli [1 ]
Helminen, Jussi [1 ]
Matikainen, Jorma [1 ]
Sipila, Jussi [1 ]
Yli-Kauhaluoma, Jari [2 ]
机构：
[1] Univ Helsinki, Organ Chem Lab, Dept Chem, FI-00014 Helsinki, Finland
[2] Univ Helsinki, Div Pharmaceut Chem, Fac Pharm, FI-00014 Helsinki, Finland
来源：
TETRAHEDRON | 2013年 / 69卷 / 02期
基金：
芬兰科学院;
关键词：
Heck; Solid-phase; Polymer; Palladium; Allylamine; Cinnamylamine; SOLID-PHASE SYNTHESIS; PALLADIUM-CATALYZED SYNTHESIS; IODO BENZYL ENAMINES; STEREOSELECTIVE ARYLATION; MEDIATED CYCLIZATIONS; COUPLING STRATEGY; TRACELESS LINKER; C-C; EFFICIENT; PALLADACYCLES;
D O I：
10.1016/j.tet.2012.10.092
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Heck reaction of Wang resin-bound allylamine with aryl iodides produces various, substituted cinnamylamines. The catalyst and additive system consisting of palladium(II) acetate, n-Bu4NOAc and potassium chloride, in addition to potassium carbonate in N,N-dimethylformamide, accomplishes a regioselective gamma-arylation. By utilising the easily formed and stable carbamate linker on Wang resin, the incompatibility of free amines with the palladium catalyst is avoided. The cinnamylamine products are cleaved from the resin with trifluoroacetic acid under mild conditions and are converted into chromatographically separable acetamides. Our solid-phase method offers a new alternative for the synthesis of cinnamylamine derivatives, as biologically interesting compounds and useful synthetic intermediates. (c) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：839 / 843
页数：5
相关论文
共 50 条
  • [31] POLYMER-SUPPORTED MEMBRANES
    ALBRECHT, O
    LASCHEWSKY, A
    MACROMOLECULES, 1984, 17 (06) : 1292 - 1293
  • [32] A polymer-supported β-ketoesterate complex of palladium as an efficient, phosphane-free, air-stable, recyclable catalyst for the Heck reaction
    Dell'Anna, MM
    Mastrorilli, P
    Muscio, F
    Nobile, CF
    Suranna, GP
    EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2002, (05) : 1094 - 1099
  • [33] Palladium(0)-catalyzed Mizoroki-Heck reaction and Rh(I)-catalyzed asymmetric hydrogenation of polymer-supported dehydroalanine system
    Doi, T
    Fujimoto, N
    Watanabe, J
    Takahashi, T
    TETRAHEDRON LETTERS, 2003, 44 (10) : 2161 - 2165
  • [34] Novel and efficient polymer supported copper catalyst for heck reaction
    Sruthi, Pambingal Rajan
    Anjali, Suresh
    Varghese, Nicy
    Anas, Saithalavi
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2020, 921
  • [35] A novel reusable polymer supported palladium catalyst for Heck reaction
    Sruthi, Pambingal Rajan
    Malini, Sivan
    Silpa, Sasi
    Anas, Saithalavi
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2025, 1025
  • [36] POLYMER-SUPPORTED MEMBRANES
    REGEN, SL
    KIRSZENSZTEJN, P
    SINGH, A
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1983, 185 (MAR): : 54 - POLY
  • [37] POLYMER-SUPPORTED CATALYSTS
    GATES, BC
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1979, (SEP): : 133 - 133
  • [38] REACTION OF ALIPHATIC DIALDEHYDES WITH CONVENTIONAL AND POLYMER-SUPPORTED WITTIG REAGENTS
    CAMPA, C
    FONT, J
    SANCHEZFERRANDO, F
    VIRGILI, A
    ANALES DE QUIMICA SERIE C-QUIMICA ORGANICA Y BIOQUIMICA, 1986, 82 (01): : 46 - 50
  • [39] Mechanism and NaOH effect of polymer-supported catalyst: phosphazene reaction
    Wu, HS
    Lee, CL
    CHEMICAL ENGINEERING JOURNAL, 2002, 90 (03) : 241 - 251
  • [40] Polymer-supported ionic liquids as catalytic reaction media.
    Winterton, N
    Davies, C
    Cooper, AI
    Xiao, JL
    Scott, K
    Basov, N
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U1523 - U1523
12345