General and efficient methodology for the Suzuki-Miyaura reaction in technical grade 2-propanol

被引:50
作者
Navarro, O
Oonishi, Y
Kelly, RA
Stevens, ED
Briel, O
Nolan, SP [1 ]
机构
[1] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA
[2] Umicore AG&Co KG, D-63403 Hanau, Germany
基金
日本学术振兴会; 美国国家科学基金会;
关键词
Suzuki-Miyaura reaction; palladium; catalysis; N-heterocyclic carbene;
D O I
10.1016/j.jorganchem.2004.04.001
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The reaction. profile of a series of palladium-based catalysts was examined in the Suzuki-Miyaura reaction using technical grade 2-propanol as solvent and potassium t-butoxide as base. The results generally show high activity. The method allows for the coupling of electron-rich aryl chlorides with sterically hindered aryl boronic acids to produce tri-ortho-substituted biaryls in high yields using very mild conditions and short reaction times. (C) 2004 Elsevier B.V. All rights reserved.
引用
收藏
页码:3722 / 3727
页数:6
相关论文
共 50 条
[21]   PdO hydrate as an efficient and recyclable catalyst for the Suzuki-Miyaura reaction in water/ethanol at room temperature [J].
Amoroso, Francesco ;
Colussi, Sara ;
Del Zotto, Alessandro ;
Llorca, Jordi ;
Trovarelli, Alessandro .
CATALYSIS COMMUNICATIONS, 2011, 12 (06) :563-567
[22]   The role of phosphines in the activations of coupled substrates in the Suzuki-Miyaura reaction [J].
Kurokhtina, A. A. ;
Larina, E. V. ;
Lagoda, N. A. ;
Schmidt, A. F. .
RUSSIAN CHEMICAL BULLETIN, 2024, 73 (03) :505-513
[23]   Palladium-catalyzed efficient Suzuki-Miyaura reaction of potassium aryltrifluoroborates in water [J].
Liu, Chun ;
Li, Xinmin ;
Wang, Xinnan ;
Jin, Zilin .
CATALYSIS COMMUNICATIONS, 2015, 69 :81-85
[24]   Highly Efficient Bulky α-Diimine Palladium Complexes for Suzuki-Miyaura Cross-Coupling Reaction [J].
Huo, Ping ;
Li, Jingbo ;
Liu, Wanyun ;
Mei, Guangquan .
CHINESE JOURNAL OF CHEMISTRY, 2017, 35 (03) :363-367
[25]   A General and Special Catalyst for Suzuki-Miyaura Coupling Processes [J].
Tang, Wenjun ;
Capacci, Andrew G. ;
Wei, Xudong ;
Li, Wenjie ;
White, Andre ;
Patel, Nitinchandra D. ;
Savoie, Jolaine ;
Gao, Joe J. ;
Rodriguez, Sonia ;
Qu, Bo ;
Haddad, Nizar ;
Lu, Bruce Z. ;
Krishnamurthy, Dhileepkumar ;
Yee, Nathan K. ;
Senanayake, Chris H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (34) :5879-5883
[26]   Application of Suzuki-Miyaura Reaction in the Chemistry of Oxolan-2-ones [J].
T. V. Ghochikyan ;
A. S. Vardanyan ;
M. A. Samvelyan ;
A. S. Galstyan ;
P. Langer .
Russian Journal of Organic Chemistry, 2019, 55 :279-281
[27]   Application of Suzuki-Miyaura Reaction in the Chemistry of Oxolan-2-ones [J].
Ghochikyan, T. V. ;
Vardanyan, A. S. ;
Samvelyan, M. A. ;
Galstyan, A. S. ;
Langer, P. .
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (02) :279-281
[28]   New, Efficient Approach for the Ligand-Free Suzuki-Miyaura Reaction of 5-Iodo-2′-deoxyuridine in Water [J].
Sartori, Guillaume ;
Herve, Gwenaelle ;
Enderlin, Gerald ;
Len, Christophe .
SYNTHESIS-STUTTGART, 2013, 45 (03) :330-333
[29]   General and highly efficient fluorinated-N-heterocyclic carbene-based catalysts for the palladium-catalyzed Suzuki-Miyaura reaction [J].
Liu, Taoping ;
Zhao, Xiaoming ;
Shen, Qilong ;
Lu, Long .
TETRAHEDRON, 2012, 68 (32) :6535-6547
[30]   Expanding the scope of the Cu assisted Suzuki-Miyaura reaction [J].
Crowley, Brendan M. ;
Potteiger, Craig M. ;
Deng, James Z. ;
Prier, Christopher K. ;
Paone, Daniel V. ;
Burgey, Christopher S. .
TETRAHEDRON LETTERS, 2011, 52 (39) :5055-5059