Sustainable Ligand-Free, Palladium-Catalyzed Suzuki–Miyaura Reactions in Water: Insights into the Role of Base
作者： Yanyan Wang , Yuanyuan Liu , Wei‐qiang Zhang , Huaming Sun , Kan Zhang
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摘要: A simple and efficient system was developed for the ligand-free Pd-catalyzed Suzuki-Miyaura reaction in water under mild conditions. Quaternary ammonium hydroxides with long chains were found to be very suitable bases. This showed improved durability Pd loadings decreased ppm level. Bases shown stabilize active palladium species addition acting as a base during catalytic process. In strong base, soluble PdII ion exhibited anti-reduction properties, which prevented aggregation deactivation of species. The entire could recycled after separating product by filtration. water-compatible air-stable effective protocol described herein represents an attractive green synthetic advance couplings.
sci-hub.se 参考文章(81)
Robert E. Mesmer, Charles F. Baes, The hydrolysis of cations ,(1976)
S. Handa, Y. Wang, F. Gallou, B. H. Lipshutz, Sustainable Fe-ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water. Science. ,vol. 349, pp. 1087- 1091 ,(2015) , 10.1126/SCIENCE.AAC6936
Ina Hoffmann, Bettina Blumenröder, Silvia Onodi neé Thumann, Sabine Dommer, Jürgen Schatz, Suzuki cross-coupling in aqueous media Green Chemistry. ,vol. 17, pp. 3844- 3857 ,(2015) , 10.1039/C5GC00794A
A. F. Shmidt, A. A. Kurokhtina, Suzuki reaction with aryl bromides at room temperature in the presence of a simple “ligand-free” catalytic system Russian Journal of Applied Chemistry. ,vol. 83, pp. 1248- 1253 ,(2010) , 10.1134/S1070427210070153
Donald A. Patrick, Mohamed A. Ismail, Reem K. Arafa, Tanja Wenzler, Xiaohua Zhu, Trupti Pandharkar, Susan Kilgore Jones, Karl A. Werbovetz, Reto Brun, David W. Boykin, Richard R. Tidwell, Synthesis and antiprotozoal activity of dicationic m-terphenyl and 1,3-dipyridylbenzene derivatives. Journal of Medicinal Chemistry. ,vol. 56, pp. 5473- 5494 ,(2013) , 10.1021/JM400508E
Marc Lamblin, Luma Nassar-Hardy, Jean-Cyrille Hierso, Eric Fouquet, François-Xavier Felpin, Recyclable Heterogeneous Palladium Catalysts in Pure Water: Sustainable Developments in Suzuki, Heck, Sonogashira and Tsuji–Trost Reactions Advanced Synthesis & Catalysis. ,vol. 352, pp. 33- 79 ,(2010) , 10.1002/ADSC.200900765
Debasree Saha, Kalicharan Chattopadhyay, Brindaban C. Ranu, Aerobic ligand-free Suzuki coupling catalyzed by in situ-generated palladium nanoparticles in water Tetrahedron Letters. ,vol. 50, pp. 1003- 1006 ,(2009) , 10.1016/J.TETLET.2008.12.063
Carin C. C. Johansson Seechurn, Matthew O. Kitching, Thomas J. Colacot, Victor Snieckus, Palladium-Catalyzed Cross-Coupling: A Historical Contextual Perspective to the 2010 Nobel Prize Angewandte Chemie. ,vol. 51, pp. 5062- 5085 ,(2012) , 10.1002/ANIE.201107017
Jesús Jover, Natalie Fey, Mark Purdie, Guy C. Lloyd-Jones, Jeremy N. Harvey, A computational study of phosphine ligand effects in Suzuki-Miyaura coupling Journal of Molecular Catalysis A-chemical. ,vol. 324, pp. 39- 47 ,(2010) , 10.1016/J.MOLCATA.2010.02.021
Árpád Molnár, Efficient, selective, and recyclable palladium catalysts in carbon-carbon coupling reactions. Chemical Reviews. ,vol. 111, pp. 2251- 2320 ,(2011) , 10.1021/CR100355B