Palladium-catalyzed cross-coupling of aroyl chlorides with aryl stannanes in the presence of triethylsilane: Efficient access to aromatic ketones

被引：2
|
作者：
Higashi, Shoko [1 ]
Uno, Sota [1 ]
Ohsuga, Yui [1 ]
Noumi, Maiko [1 ]
Saito, Ryota [1 ,2 ]
机构：
[1] Toho Univ, Fac Sci, Dept Chem, Funabashi, Chiba 2748510, Japan
[2] Toho Univ, Res Ctr Mat Integrated Properties, Funabashi, Chiba 2748510, Japan
来源：
TETRAHEDRON LETTERS | 2020年 / 61卷 / 45期
关键词：
Stille coupling reaction; Diaryl ketones; Triethylsilane; Suppression of decarbonylation; COORDINATED CARBON-MONOXIDE; SUZUKI-MIYAURA TYPE; ACID-CHLORIDES; ARYLBORONIC ACIDS; ACYL CHLORIDES; ACTIVATION; CARBONYLATION; HALIDES; ALKYL; MILD;
D O I：
10.1016/j.tetlet.2020.152466
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report the development of a palladium-catalyzed cross-coupling reaction that focuses on the preparation of aromatic ketones. Aroyl chlorides react quickly at 120 degrees C with aryl stannanes in the presence of Pd(PPh3)(4) and Et3SiH to efficiently give the corresponding ketones without the formation of significant decarbonylated byproducts. In other words, the decarbonylative side reaction is practically suppressed by simply adding Et3SiH to the reaction mixture, which reduces the amount of biaryl impurities in the products. (C) 2020 Elsevier Ltd. All rights reserved.
引用
收藏
页数：4
相关论文
共 50 条
  • [41] Palladium-Catalyzed Cross-Coupling Reaction of Alkyltrifluorosilanes with Aryl Halides
    Matsuhashi, H.
    Asai, S.
    Hirabayashi, K.
    Hatanaka, Y.
    Bulletin of the Chemical Society of Japan, 70 (02):
  • [42] Palladium-Catalyzed Hiyama Cross-Coupling Reactions of Aryl Mesylates
    Zhang, Liang
    Qing, Jiang
    Yang, Pengyuan
    Wu, Jie
    ORGANIC LETTERS, 2008, 10 (21) : 4971 - 4974
  • [43] Efficient palladium-catalyzed coupling reactions of aryl bromides and chlorides with phenols
    Hu, Tongjie
    Schulz, Thomas
    Torborg, Christian
    Chen, Xiaorong
    Wang, Jun
    Beller, Matthias
    Huang, Jun
    CHEMICAL COMMUNICATIONS, 2009, (47) : 7330 - 7332
  • [44] Palladium-catalyzed carbonylative cross-coupling of organoboranes with hypervalent iodonium salts: Synthesis of aromatic ketones
    Kang, SK
    Lim, KH
    Ho, PS
    Yoon, SK
    Son, HJ
    SYNTHETIC COMMUNICATIONS, 1998, 28 (08) : 1481 - 1489
  • [45] Palladium-catalyzed carbonylative cross-coupling of organoboranes with hypervalent iodonium salts: Synthesis of aromatic ketones
    Department of Chemistry, Sung Kyun Kwan University, Natural Science Campus, Suwon 440-746, Korea, Republic of
    Synth. Commun., 8 (1481-1489):
  • [46] PALLADIUM-CATALYZED CROSS-COUPLING REACTIONS OF CHLOROPYRAZINES WITH AROMATIC HETEROCYCLES
    AOYAGI, Y
    INOUE, A
    KOIZUMI, I
    HASHIMOTO, R
    TOKUNAGA, K
    GOHMA, K
    KOMATSU, J
    SEKINE, K
    MIYAFUJI, A
    KUNOH, J
    HONMA, R
    AKITA, Y
    OHTA, A
    HETEROCYCLES, 1992, 33 (01) : 257 - 272
  • [47] Palladium-Catalyzed Cross-Coupling of Tertiary Cyclopropyl Carbagermatranes with Acyl Chlorides
    Yang, Shuo
    Chen, Guang
    Xu, Qing-Hao
    Xiao, Bin
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (12)
  • [48] Palladium-catalyzed cross-coupling reactions of diazine N-oxides with aryl chlorides, bromides, and iodides
    Leclerc, Jean-Philippe
    Fagnou, Keith
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (46) : 7781 - 7786
  • [49] Palladium-catalyzed cross-coupling reaction of aryl(trialkyl)silanes with aryl nitriles
    Tang, Shi
    Li, Shu-Hua
    Yan, Wen-bin
    TETRAHEDRON LETTERS, 2012, 53 (50) : 6743 - 6746
  • [50] Palladium-catalyzed Carbon-Sulfur Cross-coupling Reactions of Aryl Chlorides with Indium Tris(organothiolates)
    Mo, Juntae
    Eom, Dahan
    Kim, Sung Hong
    Lee, Phil Ho
    CHEMISTRY LETTERS, 2011, 40 (09) : 980 - 982
12345