Weak Arene C-H•••O Hydrogen Bonding in Palladium-Catalyzed Arylation and Vinylation of Lactones

被引：65
|
作者：
Huang, Zhiyan [1 ]
Chen, Zuliang [1 ]
Lim, Li Hui [1 ]
Gia Chuong Phan Quang [1 ]
Hirao, Hajime [1 ]
Zhou, Jianrong [1 ]
机构：
[1] Nanyang Technol Univ, Sch Phys & Math Sci, Div Chem & Biol Chem, Singapore 637371, Singapore
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2013年 / 52卷 / 22期
基金：
新加坡国家研究基金会;
关键词：
cross-coupling; hydrogen bonds; lactones; palladium; ENANTIOSELECTIVE ALPHA-ARYLATION; SUBSTITUTED (S)-PHENYLPIPERIDINES; ASYMMETRIC ARYLATION; BRONSTED ACID; KETONES; PROTONATION; COMPLEXES; SELECTIVITY; OXIDATION; OXINDOLES;
D O I：
10.1002/anie.201300481
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Weak force in action: In the title reaction, the palladium catalyst (see figure, left) uses weak CH×××O hydrogen bonding to control the absolute configuration of the new stereocenter. A similar palladium catalyst (right) used conventional NH×××O hydrogen bonding to guide stereoselection. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：5807 / 5812
页数：6
相关论文
共 50 条
  • [21] Eco-Friendly Solvents for Palladium-Catalyzed Desulfitative C-H Bond Arylation of Heteroarenes
    Hfaiedh, Anoir
    Yuan, Kedong
    Ben Ammar, Hamed
    Ben Hassine, Bechir
    Soule, Jean-Francois
    Doucet, Henri
    CHEMSUSCHEM, 2015, 8 (10) : 1794 - 1804
  • [22] Synthesis of Asymmetrically Substituted Terpyridines by Palladium-Catalyzed Direct C-H Arylation of Pyridine N-Oxides
    Duric, Sasa
    Sypaseuth, Fanni D.
    Hoof, Santina
    Svensson, Emma
    Tzschucke, C. Christoph
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (51) : 17456 - 17463
  • [23] Palladium-Catalyzed Carbonylative C-H Activation of Heteroarenes
    Wu, Xiao-Feng
    Anbarasan, Pazhamalai
    Neumann, Helfried
    Beller, Matthias
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) : 7316 - 7319
  • [24] Recent advances in direct arylation via palladium-catalyzed aromatic C-H activation
    Li, Bi-Jie
    Yang, Shang-Dong
    Shi, Zhang-Jie
    SYNLETT, 2008, (07) : 949 - 957
  • [25] Palladium-Catalyzed Direct C-H Arylation of Arenes Promoted by Quaternary Ammonium Salt
    Yang, Sabyuk
    Hong, Soon Hyeok
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (11) : 1846 - 1851
  • [26] Orthogonal Palladium-Catalyzed Direct C-H Bond Arylation of Heteroaromatics with Aryl Halides
    Theveau, Laure
    Schneider, Cedric
    Fruit, Corinne
    Hoarau, Christophe
    CHEMCATCHEM, 2016, 8 (20) : 3183 - 3194
  • [27] Palladium-Catalyzed Domino Heck/C-H Activation/Intermolecular Direct Arylation Reactions
    Lu, Zhiyao
    Cui, Yuxin
    Jia, Yanxing
    SYNTHESIS-STUTTGART, 2011, (16): : 2595 - 2599
  • [28] Palladium-Catalyzed Direct Arylation of Azulene Based on Regioselective C-H Bond Activation
    Murai, Masahito
    Yanagawa, Mayu
    Nakamura, Masahiro
    Takai, Kazuhiko
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 5 (05) : 629 - 635
  • [29] The Cross-Selectivity in Palladium-Catalyzed Coupling of Simple Aryl C-H Bonds
    Lu, Wenjun
    SYNLETT, 2025, 36 (06) : 644 - 650
  • [30] Palladium-Catalyzed Desulfitative Direct C-H Arylation of Electron-Deficient Polyfluoroarenes with Sodium Arenesulfinates
    Miao, Tao
    Wang, Lei
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (2-3) : 429 - 436
12345