Reaction of aryl di-, tri-, or tetrabromides with arylboronic acids or alkenes in the presence of a palladium-tetraphosphine catalyst

被引:42
作者
Berthiol, F
Kondolff, I
Doucet, H
Santelli, M
机构
[1] Fac Sci & Tech St Jerome, CNRS, UMR 6180, Synth Organ Lab, F-13397 Marseille 20, France
[2] Univ Aix Marseille 3, Fac Sci St Jerome, F-13397 Marseille 20, France
关键词
tetraphosphine; palladium; Suzuki-coupling; Heck-vinylation; arylboronic acids; alkenes; aryl bromides;
D O I
10.1016/j.jorganchem.2004.06.007
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
cis, cis, cis- 1,2,3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/1/2 [PdCl(C3H5)](2) system catalyses the Suzuki and Heck reactions of aryl di-, tri-, or tetrabromides with a range of arylboronic acids or alkenes with moderate to high ratio substrate/catalyst in good yields. Aryl polybromides such as dibromobenzenes, 1,3,5-tribromobenzene, 1,2,4,5-tetrabromobenzene, dibromopyridines or a dibromothiophene have been successfully used. Convenient synthesis of a variety of di- and triarylated or vinylated compounds and even a 1,2,4,5-tetraarylated compound were prepared by use of this reaction. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:2786 / 2798
页数:13
相关论文
共 83 条
  • [11] Berthiol F, 2003, SYNLETT, P841
  • [12] Heck reaction of aryl halides with linear or cyclic alkenes catalysed by a tetraphosphine/palladium catalyst
    Berthiol, F
    Doucet, H
    Santelli, M
    [J]. TETRAHEDRON LETTERS, 2003, 44 (06) : 1221 - 1225
  • [13] Heck reaction with heteroaryl halides in the presence of a palladium-tetraphosphine catalyst
    Berthiol, F
    Feuerstein, M
    Doucet, H
    Santelli, M
    [J]. TETRAHEDRON LETTERS, 2002, 43 (32) : 5625 - 5628
  • [14] Poly-orthophenylenes:: Synthesis by Suzuki coupling and solid state helical structures
    Blake, AJ
    Cooke, PA
    Doyle, KJ
    Gair, S
    Simpkins, NS
    [J]. TETRAHEDRON LETTERS, 1998, 39 (49) : 9093 - 9096
  • [15] Bracher F, 2002, EUR J ORG CHEM, V2002, P2288, DOI 10.1002/1099-0690(200207)2002:14<2288::AID-EJOC2288>3.0.CO
  • [16] 2-G
  • [17] Brase S, 1998, EUR J ORG CHEM, V1998, P671, DOI 10.1002/(SICI)1099-0690(199804)1998:4<671::AID-EJOC671>3.0.CO
  • [18] 2-R
  • [19] α-substitution of β-thienylcarbamates:: Alkylation, vinylation and Pd-catalyzed coupling reactions
    Brugier, D
    Outurquin, F
    Paulmier, C
    [J]. TETRAHEDRON, 2000, 56 (19) : 2985 - 2993
  • [20] Asymmetric synthesis of β-amino acid scaffolds
    Bull, SD
    Davies, SG
    Smith, AD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, Royal Society of Chemistry (22): : 2931 - 2938