[Pd(IPr*OMe)(cin)Cl] (cin = Cinnamyl): A Versatile Catalyst for C-N and C-C Bond Formation

被引:82
|
作者
Bastug, Gulluzar [1 ]
Nolan, Steven P. [1 ]
机构
[1] Univ St Andrews, EaStCHEM Sch Chem, St Andrews KY16 9ST, Fife, Scotland
关键词
CROSS-COUPLING REACTIONS; ORTHO-SUBSTITUTED BIARYLS; HETEROCYCLIC CARBENE LIGANDS; SUZUKI-MIYAURA COUPLINGS; PD-PEPPSI-IPENT; BUCHWALD-HARTWIG; GRIGNARD-REAGENTS; (NHC)PD(ALLYL)CL NHC; ARYL CHLORIDES; AMINATION;
D O I
10.1021/om500026s
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
[Pd(IPr*(OMe))(cin)(Cl)] provides high catalytic activity for Buchwald-Hartwig cross-coupling reactions of sterically demanding aryl chlorides with sterically hindered and deactivated aniline derivatives. This catalyst also proved efficient in Suzuki-Miyaura reactions, thus allowing the preparation of tetra-ortho-substituted biaryls. The Kumada-Corriu coupling has also been investigated using this palladium N-heterocyclic carbene (NHC) catalyst.
引用
收藏
页码:1253 / 1258
页数:6
相关论文
共 50 条
  • [1] Carbon-Sulfur Bond Formation Catalyzed by [Pd(IPr*OMe)(cin)Cl] (cin = cinnamyl)
    Bastug, Gulluzar
    Nolan, Steven P.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18): : 9303 - 9308
  • [2] (IPr)Pd(acac)Cl: An easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation
    Marion, N
    Ecarnot, EC
    Navarro, O
    Amoroso, D
    Bell, A
    Nolan, SP
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (10): : 3816 - 3821
  • [3] [Pd(IPr*OMe)(acac)Cl]: Tuning the N-Heterocyclic Carbene in Catalytic C-N Bond Formation
    Meiries, Sebastien
    Speck, Klaus
    Cordes, David B.
    Slawin, Alexandra M. Z.
    Nolan, Steven P.
    ORGANOMETALLICS, 2013, 32 (01) : 330 - 339
  • [4] [Pd(IPr*(acac)Cl]: An Easily Synthesized, Bulky Precatalyst for C-N Bond Formation
    Meiries, Sebastien
    Chartoire, Anthony
    Slawin, Alexandra M. Z.
    Nolan, Steven P.
    ORGANOMETALLICS, 2012, 31 (08) : 3402 - 3409
  • [5] Efficient C-N and C-S Bond Formation Using the Highly Active [Ni(allyl)Cl(IPr*OMe)] Precatalyst
    Martin, Anthony R.
    Nelson, David J.
    Meiries, Sebastien
    Slawin, Alexandra M. Z.
    Nolan, Steven P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (15) : 3127 - 3131
  • [6] ALCOHOLS AS ALKYLATING AGENTS FOR C-C AND C-N BOND FORMATION
    Williams, Jonathan M. J.
    JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 2009, 52 (5-6): : 209 - 209
  • [7] Iron-Catalyzed C-C Bond Cleavage and C-N Bond Formation
    Li, Wenjuan
    Zheng, Xiaojian
    Li, Zhiping
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (01) : 181 - 190
  • [8] A versatile ruthenium catalyst for C-C bond formation by C-H bond activation
    Martinez, Remi
    Chevalier, Reynald
    Darses, Sylvain
    Genet, Jean-Pierre
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (48) : 8232 - 8235
  • [9] New methods for C-C, C-O, and C-N bond formation
    Walsh, Patrick J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [10] Supported aqueous phase catalysts for the C-C and C-N bond formation
    dos Santos, S
    Quignard, F
    Sinou, D
    Choplin, A
    PREPARATION OF CATALYSTS VII, 1998, 118 : 91 - 97