Liquid-Assisted Grinding Accelerating: Suzuki-Miyaura Reaction of Aryl Chlorides under High-Speed Ball-Milling Conditions

被引：106
作者：
Jiang, Zhi-Jiang [1 ]
Li, Zhen-Hua [2 ]
Yu, Jing-Bo [1 ]
Su, Wei-Ke [1 ]
机构：
[1] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Natl Engn Res Ctr Proc Dev Act Pharmaceut Ingredi, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Minist Educ, Key Lab Green Pharmaceut Technol & Related Equipm, Hangzhou 310014, Zhejiang, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 81卷 / 20期
基金：
中国国家自然科学基金;
关键词：
CROSS-COUPLING REACTIONS; ARYLBORONIC ACIDS; HALIDES; CONVENIENT; CATALYSIS; BASE;
D O I：
10.1021/acs.joc.6b01938
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The effect of liquid-assisted grinding has been studied using mechanical Suzuki-Miyaura reaction of aryl chlorides as the model reaction. Catalytic systems of Davephos and PCy3 are tested respectively showing strong influences from different liquids. Unexpected improvement of yield over 55% is observed using alcohols as additives, which is explained by in situ formed alkoxides and their participation in oxidative addition. Further expansion of substrates using Pd(OAc)(2)/PCy3/MeOH system gives desired products in good to high yields.
引用
收藏
页码：10049 / 10055
页数：7
相关论文
共 51 条
[11]   The Development of Versatile Methods for Palladium-Catalyzed Coupling Reactions of Aryl Electrophiles through the Use of P(t-Bu)3 and PCy3 as Ligands [J].
Fu, Gregory C. .
ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) :1555-1564
[12]   Substitution in compounds containing two or more phenyl groups. Part l. The nitration of 4-methyldiphenyl. [J].
Grieve, WSH ;
Hey, DH .
JOURNAL OF THE CHEMICAL SOCIETY, 1932, :1888-1894
[13]   Metal-catalyzed organic reactions using mechanochemistry [J].
Hernandez, Jose G. ;
Friscic, Tomislav .
TETRAHEDRON LETTERS, 2015, 56 (29) :4253-4265
[14]   Mechanochemistry [J].
James, Stuart L. ;
Friscic, Tomislav .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (18) :7494-7496
[15]   Mechanochemistry: opportunities for new and cleaner synthesis [J].
James, Stuart L. ;
Adams, Christopher J. ;
Bolm, Carsten ;
Braga, Dario ;
Collier, Paul ;
Friscic, Tomislav ;
Grepioni, Fabrizia ;
Harris, Kenneth D. M. ;
Hyett, Geoff ;
Jones, William ;
Krebs, Anke ;
Mack, James ;
Maini, Lucia ;
Orpen, A. Guy ;
Parkin, Ivan P. ;
Shearouse, William C. ;
Steed, Jonathan W. ;
Waddell, Daniel C. .
CHEMICAL SOCIETY REVIEWS, 2012, 41 (01) :413-447
[16]   Mechanochemically Activated Oxidative Coupling of Indoles with Acrylates through C-H Activation: Synthesis of 3-Vinylindoles and β,β-Diindolyl Propionates and Study of the Mechanism [J].
Jia, Kan-Yan ;
Yu, Jing-Bo ;
Jiang, Zhi-Jiang ;
Su, Wei-Ke .
JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (14) :6049-6055
[17]   i-Prl Acceleration of Negishi Cross-Coupling Reactions [J].
Kienle, Marcel ;
Knochel, Paul .
ORGANIC LETTERS, 2010, 12 (12) :2702-2705
[18]   Ligand-free palladium catalysis of aryl coupling reactions facilitated by grinding [J].
Klingensmith, LM ;
Leadbeater, NE .
TETRAHEDRON LETTERS, 2003, 44 (04) :765-768
[19]   Fast, solvent-free, highly enantioselective three-component coupling of aldehydes, alkynes, and amines catalysed by the copper(II)pybox complex under high-vibration ball-milling [J].
Li, Zhenhua ;
Jiang, Zhijiang ;
Su, Weike .
GREEN CHEMISTRY, 2015, 17 (04) :2330-2334
[20]   Microwave-assisted heterogeneous cross-coupling reactions catalyzed by nickel-in-charcoal (Ni/C) [J].
Lipshutz, Bruce H. ;
Frieman, Bryan A. ;
Lee, Ching-Tien ;
Lower, Asher ;
Nihan, Danielle M. ;
Taft, Benjamin R. .
CHEMISTRY-AN ASIAN JOURNAL, 2006, 1 (03) :417-429
123456