Palladium catalyzed asymmetric allylic alkylation using chelating N-heterocyclic carbene-amino ligands

被引:24
|
作者
Flahaut, Alexandre [1 ]
Roland, Sylvain [1 ]
Mangeney, Pierre [1 ]
机构
[1] Univ Paris 06, Chim Organ Lab, UMR 7611, Inst Chim Mol,FR 2769, F-75252 Paris 05, France
关键词
D O I
10.1016/j.tetasy.2007.01.019
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Several silver(I) complexes with chiral amino-N-heterocyclic carbene (NHC) ligands, which are not diastereomerically pure, were prepared and used to generate in situ chelating NHC-amino palladiumt(II) complexes. The potential of these palladium(II) complexes in asymmetric catalysis was evaluated in the allylic alkylation reaction. The influence of the structure and of the diastereomeric purity of the ligands on enantio selectivity, as well as the role of the silver salts, were studied. Enantiomeric excesses of up to 80% were obtained with the best ligand. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:229 / 236
页数:8
相关论文
共 50 条
  • [1] Catalytic activity of chiral chelating N-heterocyclic carbene palladium complexes towards asymmetric allylic alkylation
    Yang, Liangru
    Li, Yunfei
    Mao, Pu
    Yuan, Jinwei
    Xiao, Yongmei
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2019, 194 (08) : 780 - 788
  • [2] Chelating N-heterocyclic carbene ligands in palladium-catalyzed Heck-type reactions
    Herrmann, WA
    Reisinger, CP
    Spiegler, M
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1998, 557 (01) : 93 - 96
  • [3] A new class of chelating N-heterocyclic carbene ligands and their complexes with palladium
    Waltman, AW
    Grubbs, RH
    ORGANOMETALLICS, 2004, 23 (13) : 3105 - 3107
  • [4] Chelating Bis(N-Heterocyclic Carbene) Palladium-Catalyzed Reactions
    Liu, Ji-Quan
    Gou, Xing-Xing
    Han, Ying-Feng
    CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) : 2257 - 2276
  • [5] Palladium-catalyzed Asymmetric Allylic Alkylation Using C2-symmetric Chiral Bidentate Bis(N-heterocyclic carbene) Ligands with the o-Xylylene Framework
    Yamaguchi, Yoshitaka
    Suzuki, Yasutomo
    Matsumoto, Sawako
    Anezaki, Satoshi
    Asami, Masatoshi
    CHEMISTRY LETTERS, 2016, 45 (07) : 798 - 800
  • [6] New Bidentate Trans-Chelating N-Heterocyclic Carbene Ligands for Palladium
    Blakemore, James D.
    Chalkley, Matthew J.
    Farnaby, Joy H.
    Guard, Louise M.
    Hazari, Nilay
    Incarvito, Christopher D.
    Luzik, Eddie D., Jr.
    Suh, Hee Won
    ORGANOMETALLICS, 2011, 30 (07) : 1818 - 1829
  • [7] Synthesis of new chiral N-heterocyclic carbene-imine ligands and their application to an asymmetric allylic alkylation reaction
    Bonnet, LG
    Douthwaite, RE
    Kariuki, BM
    ORGANOMETALLICS, 2003, 22 (21) : 4187 - 4189
  • [8] Expanding Insight into Asymmetric Palladium-Catalyzed Allylic Alkylation of N-Heterocyclic Molecules and Cyclic Ketones
    Bennett, Nathan B.
    Duquette, Douglas C.
    Kim, Jimin
    Liu, Wen-Bo
    Marziale, Alexander N.
    Behenna, Douglas C.
    Virgil, Scott C.
    Stoltz, Brian M.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (14) : 4414 - 4418
  • [9] lridium/N-Heterocyclic Carbene Complex-Catalyzed Intermolecular Allylic Alkylation Reaction
    Bao, Can-Can
    Zheng, Dong-Song
    Zhang, Xiao
    You, Shu-Li
    ORGANOMETALLICS, 2018, 37 (24) : 4763 - 4772
  • [10] Synergistic N-Heterocyclic Carbene/Palladium-Catalyzed Allylation of Aldehydes with Allylic Carbonates
    Takemoto, Shunsuke
    Ishii, Takuya
    Yasuda, Shigeo
    Ohmiya, Hirohisa
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 2019, 92 (05) : 937 - 940