An Efficient Palladium Nanoparticles Catalytic System for Suzuki Coupling Reactions
- Corresponding author: Huang Jin, huahuanhuangjin@163.com Wang Wei, wangwei1987@cwnu.edu.cn
	            Citation:
	            
		            Li Hengchao, Zhao Ling, Liu Yan, Zhang Xia, Li Wangbing, Jing Linhai, Huang Jin, Wang Wei. An Efficient Palladium Nanoparticles Catalytic System for Suzuki Coupling Reactions[J]. Chinese Journal of Organic Chemistry,
							;2019, 39(11): 3207-3214.
						
							doi:
								10.6023/cjoc201904069
						
					
				
					 
				
	        
 
	                
				Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
												 doi: 10.1021/cr00039a007
											
										
				Suzuki, A. Angew. Chem.,  Int. Ed. 2011,  50, 6722.
												 doi: 10.1002/anie.201101379
											
										
				Capdeville, R.; Buchdunger, E.; Zimmermann, J.; Matter, A. Nat. Rev. Drug Discovery 2002,  1, 493.
												 doi: 10.1038/nrd839
											
										
				Corbet, J. P.; Mignani, G. Chem. Rev. 2006, 106, 2651.
												 doi: 10.1021/cr0505268
											
										
				Magano, J.; Dunetz, J. R. Chem. Rev. 2011, 111, 2177.
												 doi: 10.1021/cr100346g
											
										
				Fihri, A.; Bouhrara, M.; Nekoueishahraki, B.; Basset, J.-M.; Polshettiwar, V. Chem. Soc. Rev. 2011,  40, 5181.
												 doi: 10.1039/c1cs15079k
											
										
				(a) Jana, R.; Pathak, T. P.; Sigman, M. S. Chem. Rev. 2011, 111, 1417. 
 (b) Stockton, K. P.; Merritt, C. J.; Sumby, C. J.; Greatrex, B. W. Eur. J. Org. Chem. 2015, 6999. 
 (c) Li, J.-X.; Yang, S.-R.; Wu, W.-Q.; Jiang, H.-F. Eur. J. Org. Chem. 2018, 1284.
				Albisson, D. A.; Bedford, R. B.; Lawrence, S. E.; Scully, P. N. Chem. Commun. 1998, 2095.
										
				Zapf, A.; Ehrentraut, A.; Beller, M. Angew. Chem.,  Int. Ed. 2000,  39, 4153.
												 doi: 10.1002/1521-3773(20001117)39:22<4153::AID-ANIE4153>3.0.CO;2-T
											
										
				Yuan, D.; Huynh, H. V. Organometallics 2010,  29, 6020.
												 doi: 10.1021/om1008023
											
										
				Bianchini, C.; Lee, H. M.; Meli, A.; Oberhauser, W.; Vizza, F.; Brüggeller, P.; Rainer, H. B.; Langes, C. Chem. Commun. 2000, 777.
										
				Nair, P.; Anderson, G. K.; Rath, N. P. Organometallics 2003, 22, 1494.
												 doi: 10.1021/om0209069
											
										
				Imamoto, T.; Yashio, K.; Crépy, K. V. L.; Katagiri, K.; Takahashi, H.; Kouchi, M.; Gridnev, I. D. Organometallics 2006,  25, 908.
												 doi: 10.1021/om050759p
											
										
				Field, L. D.; Messerle, B. A.; Smernik, R. J.; Hambley, T. W.; Turner, P. Inorg. Chem. 1997,  36, 2884.
												 doi: 10.1021/ic970030b
											
										
				(a) Laurenti, D.; Feuerstein, M.; Pèpe, G.; Doucet, H.; Santelli, M. J. Org. Chem. 2001, 66, 1633.
 (b) Feuerstein, M.; Laurenti, D.; Bougeant, C.; Doucet, H.; Santelli, M. Chem. Commun. 2001, 325.
 (c) Feuerstein, M.; Doucet, H.; Santelli, M. Synlett 2001, 9, 1458.
 (d) Feuerstein, M.; Doucet, H.; Santelli, M. Tetrahedron Lett. 2001, 42, 6667.
 (e) Feuerstein, M.; Doucet, H.; Santelli, M. J. Organomet. Chem. 2003, 687, 327.
				Hierso, J.-C.; Fihri, A.; Amardeil, R.; Meunier, P.; Doucet, H.; Santelli, M.; Donnadieu, B. Organometallics 2003,  22, 4490.
												 doi: 10.1021/om0302948
											
										
				Zaborova, E.; Deschamp, J.; Guieu, S.; Bleriot, Y.; Poli, G.; Menand, M.; Madec, D.; Prestat, G.; Sollogoub, M. Chem. Commun. 2011,  47, 9206.
												 doi: 10.1039/c1cc12241j
											
										
				(a) Wang, K.; Yi, T.; Yu, X.-J.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Appl. Organomet. Chem. 2012, 26, 342.
 (b) Wang, K.; Fu, Q.; Zhou, R.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Appl. Organomet. Chem. 2013, 27, 232.
 (c) Wang, K.; Wang, W.; Luo, H.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Catal. Lett. 2013, 143, 1214.
 (d) Guo, F.-C.; Zhou, R.; Jiang, Z.-J.; Wang, W.; Zheng, X.-L.; Fu, H.-Y.; Chen, H.; Li, R.-X. Catal. Commun. 2015, 66, 87.
				Arumugam, V.; Kaminsky, W.; Bhuvanesh, N. S. P.; Nallasamy, D. RSC Adv. 2015,  5, 59428.
												 doi: 10.1039/C5RA10973F
											
										
				Jansa, J.; Jambor, R. Appl. Organomet. Chem. 2016,  30, 1036.
												 doi: 10.1002/aoc.3539
											
										
				Ahmed, J.; Chakraborty, S.; Jose, A.; Mandal, S. K. J. Am. Chem. Soc. 2018,  140, 8330.
												 doi: 10.1021/jacs.8b04786
											
										
				Klein, M.; Voigtmann, U.; Haack, T.; Erdinger, L.; Boche, G. Mutat. Res. 2000,  467, 55.
												 doi: 10.1016/S1383-5718(00)00012-7
											
										
				Macé, Y.; Raymondeau, B.; Pradet, C.; Blazejewski, J. C.; Magnier, E. Eur. J. Org. Chem. 2009, 1390.
										
				Ernst, J. B.; Rakers, L.; Glorius, F. Synthesis 2017,  49, 260.
										
				Duan, X.-Y.; Li, P.-B.; Zhu, G.-R.; Fu, C.-L.; Chen, Q.; Huang, X.; Ma, S.-M. Org. Chem. Front. 2018,  5, 3319.
												 doi: 10.1039/C8QO00781K
											
										
				Chiu, C. C.; Chiu, H. T.; Lee, D. S.; Lu, T. J. RSC Adv. 2018, 8, 26407.
												 doi: 10.1039/C8RA04094J
											
										
 
						
						
						
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Reaction conditions: 1a (0.5 mmol), 2a (1.0 mmol), [Pd(C3H5)Cl]2 (0.0005 mmol), K2CO3 (1.0 mmol), DMF (1.0 mL), TBAB (0.125 mmol), under argon, 100 ℃). (■) Control experiment; (○) Hg(0) (0.5 mmol) poisoning experiment