The highly efficient Suzuki–Miyaura cross-coupling reaction using cyclopalladated N-alkylferrocenylimine as a catalyst in aqueous medium at room temperature under ambient atmosphere

作者: Bing Mu , Tiesheng Li , Jingya Li , Yangjie Wu

DOI: 10.1016/J.JORGANCHEM.2008.01.012

关键词: Base (chemistry)Polymer chemistryChemistryPhotochemistryCoupling reactionDimerHalideCatalysisAlkylPhenylboronic acidArylPhysical and Theoretical ChemistryInorganic chemistryOrganic chemistryMaterials ChemistryBiochemistry

摘要: Abstract A series of N -alkyl-substituted cyclopalladated ferrocenylimines were used in palladium-catalyzed Suzuki–Miyaura cross-coupling reactions aryl halides room temperature and CH 3 OH/H 2 O media under aerobic conditions. As for the catalysts, length -alkyl chains has no significant effect on catalytic activity. Using 0.01 mol% dimer 3a presence K CO as base offered excellent yields reaction activated non-activated bromides with phenylboronic acid.

参考文章(51)
Günther Oehme, Ingrid Grassert, Eckhard Paetzold, Roland Meisel, Kerstin Drexler, Hans Fuhrmann, Complex catalyzed hydrogenation and carbon–carbon bond formation in aqueous micelles Coordination Chemistry Reviews. pp. 585- 600 ,(1999) , 10.1016/S0010-8545(99)00012-0
Fu-Yu Tsai, Bo-Nan Lin, Ming-Jie Chen, Chung-Yuan Mou, Shiuh-Tzung Liu, None, Anchored palladium bipyridyl complex in nanosized MCM-41: a recyclable and efficient catalyst for the Kumada–Corriu reaction Tetrahedron. ,vol. 63, pp. 4304- 4309 ,(2007) , 10.1016/J.TET.2007.03.046
N. A. Bumagin, V. V. Bykov, I. P. Beletskaya, Synthesis of diaryls from phenylboric acid and aryl iodides in an aqueous medium Russian Chemical Bulletin. ,vol. 38, pp. 2206- 2206 ,(1989) , 10.1007/BF00962156
Chao Jun. Li, Organic reactions in aqueous media - with a focus on carbon-carbon bond formation Chemical Reviews. ,vol. 93, pp. 2023- 2035 ,(1993) , 10.1021/CR00022A004
Antonio Arcadi, Giorgio Cerichelli, Marco Chiarini, Mariano Correa, Daniel Zorzan, A Mild and Versatile Method for Palladium‐Catalyzed Cross‐Coupling of Aryl Halides in Water and Surfactants European Journal of Organic Chemistry. ,vol. 2003, pp. 4080- 4086 ,(2003) , 10.1002/EJOC.200300356
Zuhui Zhang, Zhiyong Wang, Diatomite-supported Pd nanoparticles: an efficient catalyst for Heck and Suzuki reactions. Journal of Organic Chemistry. ,vol. 71, pp. 7485- 7487 ,(2006) , 10.1021/JO061179K
Lei Wu, Bao-Lin Li, Yi-Yong Huang, Hai-Feng Zhou, Yan-Mei He, Qing-Hua Fan, Phosphine Dendrimer-Stabilized Palladium Nanoparticles, a Highly Active and Recyclable Catalyst for the Suzuki−Miyaura Reaction and Hydrogenation Organic Letters. ,vol. 8, pp. 3605- 3608 ,(2006) , 10.1021/OL0614424
Manfred T. Reetz, Elke Westermann, Phosphane-Free Palladium-Catalyzed Coupling Reactions: The Decisive Role of Pd Nanoparticles Angewandte Chemie International Edition. ,vol. 39, pp. 165- 168 ,(2000) , 10.1002/(SICI)1521-3773(20000103)39:1<165::AID-ANIE165>3.0.CO;2-B
Shū Kobayashi, Kei Manabe, Green Lewis acid catalysis in organic synthesis Pure and Applied Chemistry. ,vol. 72, pp. 1373- 1380 ,(2000) , 10.1351/PAC200072071373