Monodentate Phosphorus Ligand-Enabled General Palladium-Catalyzed Allylic C-H Alkylation of Terminal Alkenes

被引:34
|
作者
Fan, Lian-Feng [1 ,2 ]
Wang, Pu-Sheng [1 ,2 ]
Gong, Liu-Zhu [1 ,2 ]
机构
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
关键词
FUNCTIONALIZATION; PHOSPHORAMIDITES; OLEFINS; PYRAZOL-5-ONES; ALLYLATION; OXIDATION; STRATEGY; COMPLEX;
D O I
10.1021/acs.orglett.9b02325
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Monodentate phosphorus ligands have been found to enable the palladium-catalyzed allylic C-H alkylation reaction of terminal alkenes with a wide variety of carbon nucleophiles. Moreover, an asymmetric allylic C-H alkylation of terminal alkenes with pyrazol-5-ones has been established in the presence of chiral phosphoramidite ligand and chiral phosphoric acid as co-catalyst. Mechanistic studies suggest that a ternary Pd(0) complex, coordinated with a monodentate phosphorus ligand, benzoquinone, and alkene, is most likely to be an active species.
引用
收藏
页码:6720 / 6725
页数:6
相关论文
共 50 条
  • [21] Photoinduced palladium-catalyzed asymmetric allylic C-H amination
    Wei, Yi
    Xiong, Fen-Ya
    Lu, Liang-Qiu
    Xiao, Wen-Jing
    [J]. CHEM, 2023, 9 (03): : 559 - 561
  • [22] Palladium-Catalyzed Allylic C-H Bond Functionalization of Olefins
    Liu, Guosheng
    Wu, Yichen
    [J]. C-H ACTIVATION, 2010, 292 : 195 - 209
  • [23] Mechanistic Investigation of Palladium-Catalyzed Allylic C-H Activation
    Engelin, Casper
    Jensen, Thomas
    Rodriguez-Rodriguez, Sergio
    Fristrup, Peter
    [J]. ACS CATALYSIS, 2013, 3 (03): : 294 - 302
  • [24] Palladium-Catalyzed Allylic Acyloxylation of Terminal Alkenes in the Presence of a Base
    Thiery, Emilie
    Aouf, Chahinez
    Belloy, Julien
    Harakat, Dominique
    Le Bras, Jean
    Muzart, Jacques
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05): : 1771 - 1774
  • [25] Palladium-Catalyzed Regioselective C-H Iodination of Unactivated Alkenes
    Schreib, Benedikt S.
    Carreira, Erick M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (22) : 8758 - 8763
  • [26] Palladium(II) catalyzed allylic C-H alkylation of unactivated α-olefins
    Young, Andrew J.
    White, M. Christina
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [27] Ligand-Enabled Arylation of -C-H Bonds
    Li, Suhua
    Zhu, Ru-Yi
    Xiao, Kai-Jiong
    Yu, Jin-Quan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (13) : 4317 - 4321
  • [28] Ligand effects in palladium-catalyzed allylic alkylation in ionic liquids
    Ross, J
    Chen, WP
    Xu, LJ
    Xiao, JL
    [J]. ORGANOMETALLICS, 2001, 20 (01) : 138 - 142
  • [29] Access to Fluorinated Quaternary Stereogenic Centers via Palladium-Catalyzed Asymmetric Allylic C-H Alkylation
    Wei, Jia-Hui
    Jin, You-Xiang
    Wang, Pu-Sheng
    Gong, Liu-Zhu
    [J]. SYNLETT, 2023, 34 (20) : 2411 - 2416
  • [30] Transient Ligand-Enabled Transition Metal-Catalyzed C-H Functionalization
    Niu, Ben
    Yang, Ke
    Lawrence, Brianna
    Ge, Haibo
    [J]. CHEMSUSCHEM, 2019, 12 (13) : 2955 - 2969