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
  • [21] Palladium-Catalyzed Cross-Coupling of Aryl Bromides and Chlorides with Trimethylsilylalkynes under Mild Conditions
    Tlahuext-Aca, Adrian
    Nguyen, Quyen D.
    Gao, Yang
    Sati, Girish C.
    Zhao, Jinpeng
    Valco, Daniel
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (18): : 13762 - 13767
  • [22] Palladium-catalyzed cross-coupling reactions of aryl mesylates
    So, Chau Ming
    Kwong, Fuk Yee
    CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) : 4963 - 4972
  • [23] Palladium-catalyzed cross-coupling of aryl halides with acylsilanes
    Schmink, Jason R.
    Krska, Shane W.
    Tudge, Matthew T.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [24] Arylation of α-Chiral Ketones by Palladium-Catalyzed Cross-Coupling Reactions of Tosylhydrazones with Aryl Halides
    Barluenga, Jose
    Escribano, Maria
    Aznar, Fernando
    Valdes, Carlos
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (38) : 6856 - 6859
  • [25] PALLADIUM-CATALYZED CROSS-COUPLING OF VINYLALANES WITH ARYL HALIDES
    ALHASSAN, MI
    SYNTHETIC COMMUNICATIONS, 1987, 17 (12) : 1413 - 1420
  • [26] An efficient palladium-catalyzed Heck coupling of aryl chlorides with alkenes
    Yi, CY
    Hua, RM
    TETRAHEDRON LETTERS, 2006, 47 (15) : 2573 - 2576
  • [27] A new method for the synthesis of ketones: The palladium-catalyzed cross-coupling of acid chlorides with arylboronic acids
    Haddach, M
    McCarthy, JR
    TETRAHEDRON LETTERS, 1999, 40 (16) : 3109 - 3112
  • [28] Palladium-catalyzed chemoselective cross-coupling of acyl chlorides and organostannanes
    Lerebours, R
    Camacho-Soto, A
    Wolf, C
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21): : 8601 - 8604
  • [29] Palladium-catalyzed cross-coupling of aryl chlorides with O, N-chelate stabilized diarylborinates
    Zhang, Nan
    Wang, Chen
    Zou, Gang
    Tang, Jie
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 842 : 54 - 58
  • [30] PALLADIUM CATALYZED CROSS-COUPLING OF ALPHA-ALKOXY(AMINO) STANNANES WITH ACYL CHLORIDES
    BHATT, RH
    YE, J
    FALCK, JR
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 : 63 - ORGN
12345