Ruphos-mediated Suzuki cross-coupling of secondary alkyl trifluoroborates

被引:53
作者
van den Hoogenband, Adri [1 ]
Lange, Jos H. M. [1 ]
Terpstra, Jan Willem [1 ]
Koch, Melle [2 ]
Visser, Gerben M. [2 ]
Visser, Martin [1 ]
Korstanje, Ties J. [1 ]
Jastrzebski, Johann T. B. H. [3 ]
机构
[1] Solvay Pharmaceut, Res Labs, NL-1381 CP Weesp, Netherlands
[2] Wageningen Univ, Organ Chem Lab, NL-6703 HB Wageningen, Netherlands
[3] Univ Utrecht, NL-3584 CH Utrecht, Netherlands
关键词
D O I
10.1016/j.tetlet.2008.04.129
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A Ruphos-mediated Suzuki cross-coupling between (hetero)aryl bromides and secondary alkyltrifluoroborates is described using palladium catalysis. The Ruphos ligand showed superior properties as compared to S-Phos in this type of reaction. This method constitutes a valuable extension to current methods for the straightforward production of secondary-alkylated (hetero)aryl derivatives. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4122 / 4124
页数:3
相关论文
共 73 条
  • [61] Carbon-carbon bonding made easy
    Suzuki, A
    [J]. CHEMICAL COMMUNICATIONS, 2005, (38) : 4759 - 4763
  • [62] Cross-coupling reactions via organoboranes
    Suzuki, A
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) : 83 - 90
  • [63] A novel methodology for efficient removal of residual palladium from a product of the Suzuki-Miyaura coupling with polymer-supported ethylenediamine derivatives
    Urawa, Y
    Miyazawa, M
    Ozeki, N
    Ogura, K
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2003, 7 (02) : 191 - 195
  • [64] An efficient one-pot synthesis of novel 4-aryl-1-methyloxindoles
    van den Hoogenband, Adri
    Lange, Jos H. M.
    Iwema-Bakker, Wouter I.
    den Hartog, Jack A. J.
    van Schaik, Jord
    Feenstra, Rolf W.
    Terpstra, Jan Willem
    [J]. TETRAHEDRON LETTERS, 2006, 47 (26) : 4361 - 4364
  • [65] Use of tunable ligands allows for intermolecular Pd-catalyzed C-O bond formation
    Vorogushin, AV
    Huang, XH
    Buchwald, SL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (22) : 8146 - 8149
  • [66] A rationally designed universal catalyst for Suzuki-Miyaura coupling processes
    Walker, SD
    Barder, TE
    Martinelli, JR
    Buchwald, SL
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (14) : 1871 - 1876
  • [67] Cyclopropylboronic acid: synthesis and Suzuki cross-coupling reactions
    Wallace, DJ
    Chen, CY
    [J]. TETRAHEDRON LETTERS, 2002, 43 (39) : 6987 - 6990
  • [68] Cross-coupling reaction of cyclopropylboronic acid with bromoarenes
    Wang, XZ
    Deng, MZ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1996, (22): : 2663 - 2664
  • [69] Palladium-catalyzed Suzuki-Miyaura couplings of potassium aryl trifluoroborates with 4-tosyloxycoumarins or 4-tosyloxyquinolin-2(1H)-one
    Wu, J
    Zhang, LA
    Xia, HG
    [J]. TETRAHEDRON LETTERS, 2006, 47 (10) : 1525 - 1528
  • [70] Yao ML, 2000, SYNTHESIS-STUTTGART, P1095