Ligand-Enabled Gold-Catalyzed C(sp2)-O Cross-Coupling Reactions

被引:34
|
作者
Das, Avishek [1 ]
Patil, Nitin T. [1 ]
机构
[1] Indian Inst Sci Educ & Res Bhopal, Dept Chem, Bhopal 462066, India
关键词
gold catalysis; oxidative addition; reductive elimination; C-O cross-coupling; methoxylation; aryl alkyl ethers; O BOND FORMATION; ACTIVATED ARYL; BROMIDES; HALIDES; ETHYNYLBENZIODOXOLONES; HYDROXYLATION; REACTIVITY; COMPLEXES; CHEMISTRY; IODIDES;
D O I
10.1021/acscatal.3c00338
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Reported herein is a ligand-enabled gold-catalyzed C(sp2)-O cross-coupling reaction of aryl iodides and aliphatic alcohols. The synthesis of a variety of aryl alkyl ethers including complex biomolecules and various medicinally relevant motifs has been achieved to demonstrate the usefulness of the method. The importance of gold catalysis has been highlighted by overcoming the selectivity issues that are in general observed for C-O cross -coupling reactions when other transition metals are used as catalysts. + R -OH R = alkyl ./ 63 examples OR Au iota CI* 4,/ 50 -99% yields o Directing group free o Mild reaction conditions 0 Electron-poor Ad preferred over electron-rich An N III NMe2 PAd2
引用
收藏
页码:3847 / 3853
页数:7
相关论文
共 50 条
  • [21] Boryl radicals facilitate C(sp2)-C(sp3) cross-coupling reactions
    Rodrigalvarez, Jesus
    Martin, Ruben
    NATURE SYNTHESIS, 2024, 3 (10): : 1188 - 1189
  • [22] Highly stable magnetically separable copper nanocatalyst as an efficient catalyst for C(sp2)-C(sp) and C(sp2)-C(sp2) cross-coupling reactions
    Keypour, Hassan
    Balali, Masomeh
    Nejat, Razieh
    Bagherzadeh, Mojtaba
    APPLIED ORGANOMETALLIC CHEMISTRY, 2017, 31 (09)
  • [23] Gold-Catalyzed Oxidative Biaryl Cross-Coupling of Organometallics
    Liu, Kai
    Li, Nian
    Ning, Yunyun
    Zhu, Chengjian
    Xie, Jin
    CHEM, 2019, 5 (10): : 2718 - 2730
  • [24] Recent Advance in Ni-Catalyzed Reductive Cross-Coupling to Construct C(sp2)-C(sp2) and C(sp2)-C(sp3) Bonds
    Li, Yaqiong
    Fan, Yuhang
    Jia, Qianfa
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (02) : 350 - 362
  • [25] Ligand-enabled cross-coupling of C(sp3)-H bonds with arylboron reagents via Pd(II)/Pd(o) catalysis
    Chan, Kelvin S. L.
    Wasa, Masayuki
    Chu, Ling
    Laforteza, Brian N.
    Miura, Masanori
    Yu, Jin-Quan
    NATURE CHEMISTRY, 2014, 6 (02) : 146 - 150
  • [26] Ligand-Free Iron-Catalyzed Carbon(sp2)-Carbon(sp2) Cross-Coupling of Alkenyllithium with Vinyl Halides
    Liu, Qiang
    Wang, Zhi-Yong
    Peng, Xiao-Shui
    Wong, Henry N. C.
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (12): : 6325 - 6333
  • [27] C(sp2)-C(sp2) Suzuki cross-coupling of arylammonium salts catalyzed by a stable Pd-NHC complex
    Tang, Huiling
    Liu, Mengna
    Zhu, Meiqi
    Cui, Benqiang
    Shi, Yanhui
    Cao, Changsheng
    TETRAHEDRON, 2021, 98
  • [28] Cobalt-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions of Diarylmanganese Reagents with Secondary Alkyl Iodides
    Hofmayer, Maximilian S.
    Hammann, Jeffrey M.
    Haas, Diana
    Knochel, Paul
    ORGANIC LETTERS, 2016, 18 (24) : 6456 - 6459
  • [29] Copper-catalyzed C(sp2)-C(sp) Sonogashira-type cross-coupling reactions accelerated by polycyclic aromatic hydrocarbons
    Xu, Wei
    Yu, Bo
    Sun, Huaming
    Zhang, Guofang
    Zhang, Weiqiang
    Gao, Ziwei
    APPLIED ORGANOMETALLIC CHEMISTRY, 2015, 29 (06) : 353 - 356
  • [30] Nickel-Catalyzed Electrochemical C(sp3)-C(sp2) Cross-Coupling Reactions of Benzyl Trifluoroborate and Organic Halides**
    Luo, Jian
    Hu, Bo
    Wu, Wenda
    Hu, Maowei
    Liu, T. Leo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (11) : 6107 - 6116