Pd-catalyzed allylic substitution using nucleophilic N-heterocyclic carbene as a ligand

被引：52
|
作者：
Sato, Y [1 ]
Yoshino, T [1 ]
Mori, M [1 ]
机构：
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 01期
关键词：
D O I：
10.1021/ol026961v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A nucleophilic N-heterocyclic carbene has been successfully used in a Pd(0)-catalyzed allylic substitution for the first time. It was found that allylic substitution with a soft nucleophile using a Pd-carbene catalyst proceeds via retention of configuration, the stereochemical reaction pathway being the same as that of the reaction using a Pd-phosphine complex.
引用
收藏
页码：31 / 33
页数：3
相关论文
共 50 条
  • [41] N-Heterocyclic Carbene Dichotomy in Pd-Catalyzed Acylation of Aryl Chlorides via C-H Bond Functionalization
    Flores-Gaspar, Areli
    Gutierrez-Bonet, Alvaro
    Martin, Ruben
    ORGANIC LETTERS, 2012, 14 (20) : 5234 - 5237
  • [42] γ-selective allylic substitution reaction with Grignard reagents catalyzed by copper N-heterocyclic carbene complexes and its application to enantioselective synthesis
    Tominaga, S
    Oi, Y
    Kato, T
    An, DK
    Okamoto, S
    TETRAHEDRON LETTERS, 2004, 45 (29) : 5585 - 5588
  • [43] N-Heterocyclic Carbene Catalyzed Domino Reactions
    Grossmann, Andre
    Enders, Dieter
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (02) : 314 - 325
  • [44] N-Heterocyclic carbene-catalyzed oxidations
    Maki, Brooks E.
    Chan, Audrey
    Phillips, Eric M.
    Scheidt, Karl A.
    TETRAHEDRON, 2009, 65 (16) : 3102 - 3109
  • [45] N-Heterocyclic Carbene Catalyzed Hydrophosphonylation of Aldehydes
    Cai, Zhi-Hua
    Du, Guang-Fen
    He, Lin
    Gu, Cheng-Zhi
    Dai, Bin
    SYNTHESIS-STUTTGART, 2011, (13): : 2073 - 2078
  • [46] Development of enantioselective Cu-catalyzed allylic oxidation reactions with N-heterocyclic carbene ligands
    Morrison, Ryan J.
    Khubchandani, Nisha A.
    Lombardi, Pamela J.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [47] Pd(0)-catalyzed bismetallative cyclization of enynes in the presence of Bu3SnSiMe3 using N-heterocyclic carbene as a ligand
    Sato, Y
    Imakuni, N
    Mori, M
    ADVANCED SYNTHESIS & CATALYSIS, 2003, 345 (04) : 488 - 491
  • [48] Regioselective allylic alkylation and etherification catalyzed by in situ generated N-heterocyclic carbene ruthenium complexes
    Gürbüz, N
    Özdemir, I
    Çetinkaya, B
    Renaud, JL
    Demerseman, B
    Bruneau, C
    TETRAHEDRON LETTERS, 2006, 47 (04) : 535 - 538
  • [49] N-Heterocyclic carbene catalyzed intramolecular nucleophilic addition of carbonyl anion equivalents to enol ethers
    He, Jinmei
    Tang, Shouchu
    Liu, Jian
    Su, Yingpeng
    Pan, Xinfu
    She, Xuegong
    TETRAHEDRON, 2008, 64 (37) : 8797 - 8800
  • [50] Hydrogen bonding for regiocontrol in the Pd-catalyzed allylic substitution.
    Cook, GR
    Yu, H
    Sankaranarayanan, S
    Shanker, PS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U141 - U141
12345