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
  • [1] PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL CHLORIDES WITH ARYLSILATRANES
    Yamamoto, Yutaro
    Baralle, Alexandre
    Godefroy, Anais
    Murakami, Kei
    Yorimitsu, Hideki
    Osuka, Atsuhiro
    HETEROCYCLES, 2017, 95 (01) : 568 - 574
  • [2] Palladium-catalyzed cross-coupling reaction of silicone with aryl chlorides
    Koike, T
    Mori, A
    SYNLETT, 2003, (12) : 1850 - 1852
  • [3] Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Tosylates with Hydrazine
    Lundgren, Rylan J.
    Stradiotto, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (46) : 8686 - 8690
  • [4] Palladium-Catalyzed Cross-Coupling of Aryl Chlorides and Tosylates with Hydrazine
    Lundgren, Rylan J.
    Stradiotto, Mark
    SYNTHESIS-STUTTGART, 2011, (01): : A3 - A5
  • [5] POLY(ARYL KETONES) VIA PALLADIUM-CATALYZED CROSS-COUPLING
    MOORE, JS
    MAKROMOLEKULARE CHEMIE-RAPID COMMUNICATIONS, 1992, 13 (02): : 91 - 96
  • [6] Palladium-Catalyzed Hiyama Cross-Coupling of Aryltrifluorosilanes with Aryl and Heteroaryl Chlorides
    Molander, Gary A.
    Iannazzo, Laura
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (21): : 9182 - 9187
  • [7] An atom-efficient palladium-catalyzed cross-coupling reaction of triarylbismuths with acid chlorides: synthesis of diaryl and alkyl aryl ketones
    Rao, Maddah L. N.
    Venkatesh, Varadhachari
    Jadhav, Deepak N.
    TETRAHEDRON LETTERS, 2006, 47 (39) : 6975 - 6978
  • [8] Preparation of ketones via the palladium-catalyzed cross-coupling of acid chlorides with trialkylboranes
    Kabalka, GW
    Malladi, RR
    Tejedor, D
    Kelley, S
    TETRAHEDRON LETTERS, 2000, 41 (07) : 999 - 1001
  • [9] A General Palladium-Catalyzed Hiyama Cross-Coupling Reaction of Aryl and Heteroaryl Chlorides
    Yuen, On Ying
    So, Chau Ming
    Man, Ho Wing
    Kwong, Fuk Yee
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (19) : 6471 - 6476
  • [10] Stereospecific palladium-catalyzed cross-coupling of (E)- and (Z)-alkenylsilanolates with aryl chlorides
    Denmark, Scott E.
    Kallemeyn, Jeffrey M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (50) : 15958 - 15959
12345