Pd/P(i-BuNCH2CH2)3N:: an efficient catalyst for Suzuki cross-coupling of aryl bromides and chlorides with arylboronic acids

被引:82
作者
Urgaonkar, S [1 ]
Nagarajan, M [1 ]
Verkade, JG [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
基金
美国国家科学基金会;
关键词
cross-coupling reaction; ligands; bicyclic triaminophosphine;
D O I
10.1016/S0040-4039(02)02189-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pd(OAc)(2) in combination with the commercially available ligand P(i-BuNCH2CH2)(3)N catalyzes the Suzuki cross-coupling reaction of a wide variety of aryl bromides and chlorides with arylboronic acids, affording the desired biaryls in excellent yields. It has also been shown that P(NMe2)(3) can be employed as a ligand, though with significantly more limited success. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8921 / 8924
页数:4
相关论文
共 22 条
  • [1] Palladium/P,O-ligand-catalyzed Suzuki cross-coupling reactions of arylboronic acids and aryl chlorides. Isolation and structural characterization of (P,O)-Pd(dba) complex
    Bei, XH
    Turner, HW
    Weinberg, WH
    Guram, AS
    Petersen, JL
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (18) : 6797 - 6803
  • [2] PALLADACYCLES AS EFFICIENT CATALYSTS FOR ARYL COUPLING REACTIONS
    BELLER, M
    FISCHER, H
    HERRMANN, WA
    OFELE, K
    BROSSMER, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17): : 1848 - 1849
  • [3] N-heterocyclic carbenes Part 26.: N-heterocyclic carbene complexes of palladium(0):: synthesis and application in the Suzuki cross-coupling reaction
    Böhm, VPW
    Gstöttmayr, CWK
    Weskamp, T
    Herrmann, WA
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2000, 595 (02) : 186 - 190
  • [4] Synthesis of bulky, electron rich hemilabile phosphines and their application in the Suzuki coupling reaction of aryl chlorides
    Clarke, ML
    Cole-Hamilton, DJ
    Woollins, JD
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 2001, (19): : 2721 - 2723
  • [5] P-N bond formation as a route to highly electron rich phosphine ligands
    Clarke, ML
    Cole-Hamilton, DJ
    Slawin, AMZ
    Woollins, JD
    [J]. CHEMICAL COMMUNICATIONS, 2000, (20) : 2065 - 2066
  • [6] CROWLEY AH, 1982, INORG CHEM, V21, P543
  • [7] Suzuki-Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems
    Grasa, GA
    Viciu, MS
    Huang, JK
    Zhang, CM
    Trudell, ML
    Nolan, SP
    [J]. ORGANOMETALLICS, 2002, 21 (14) : 2866 - 2873
  • [8] TRANSFORMATIONS OF CHLOROARENES, CATALYZED BY TRANSITION-METAL COMPLEXES
    GRUSHIN, VV
    ALPER, H
    [J]. CHEMICAL REVIEWS, 1994, 94 (04) : 1047 - 1062
  • [9] Versatile catalysts for the Suzuki cross-coupling of arylboronic acids with aryl and vinyl halides and triflates under mild conditions
    Littke, AF
    Dai, CY
    Fu, GC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (17) : 4020 - 4028
  • [10] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF ORGANOBORON COMPOUNDS
    MIYAURA, N
    SUZUKI, A
    [J]. CHEMICAL REVIEWS, 1995, 95 (07) : 2457 - 2483