Copper-Catalyzed Aerobic Oxidation Reaction of Benzyl Alcohol in Water under Base-Free Condition
- Corresponding author: Mao Jincheng, jcmao@swpu.edu.cn
	            Citation:
	            
		            Yang Xiaojiang, Mao Jincheng, Zhang Heng, Zhang Yang, Mao Jinhua. Copper-Catalyzed Aerobic Oxidation Reaction of Benzyl Alcohol in Water under Base-Free Condition[J]. Chinese Journal of Organic Chemistry,
							;2018, 38(10): 2780-2783.
						
							doi:
								10.6023/cjoc201802018
						
					
				
					 
				
	        
 
	                
				Liu, W. X.; Wu, Y. Q.; Li, L. Z.; Li, X. Chin. J. Org. Chem. 2016, 36, 1501(in Chinese).
										 
				Luo, F. H.; Long, Y.; Li, Z. K.; Zhou, X. G. Acta Chim. Sinica 2016, 74, 805(in Chinese).
												 doi: 10.3866/PKU.WHXB201603111
											
										
				Chen, Y.; Hu, A. H.; Yang, L. Y.; Li, Z. Y.; Yan, K. Chin. J. Org. Chem. 2017, 37, 1939(in Chinese).
										 
				Bowden, K.; Heilbron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39.
												 doi: 10.1039/jr9460000039
											
										
				Corey, E. J.; Suggs, J. W. Tetrahedron Lett. 1975, 16, 2647.
												 doi: 10.1016/S0040-4039(00)75204-X
											
										
				Piancatelli, G.; Scettri, A.; Auria, M. Synthesis 1982, 245.
										 
				De, A. J. Sci. Ind. Res. 1982, 41, 484.
										
				Luzzio, F. A.; Guziec, F. S. Org. Prep. Proced. Int. 1988, 20, 533.
												 doi: 10.1080/00304948809356301
											
										
				Ladbury, J. W.; Cullis, C. F. Chem. Rev. 1958, 58, 403.
												 doi: 10.1021/cr50020a005
											
										
				Fatiadi, A. J. Synthesis 1976, 65.
										
				Taylor, R. J. K.; Reid, M.; Foot, J.; Raw, S. A. Acc. Chem. Res. 2005, 38, 851.
												 doi: 10.1021/ar050113t
											
										
				Semmelhack, M. F.; Schmid, C. R.; Cortes, D. A.; Chou, C. S. J. Am. Chem. Soc. 1984, 106, 3374.
												 doi: 10.1021/ja00323a064
											
										
				Gamez, P.; Arends, I. W. C. E.; Sheldon, R. A.; Reedijk, J. Adv. Synth. Catal. 2004, 346, 805.
												 doi: 10.1002/(ISSN)1615-4169
											
										
				Jiang, N.; Ragauskas, A. J. J. Org. Chem. 2006, 71, 7087.
												 doi: 10.1021/jo060837y
											
										
				Figiel, P. J.; Sibaouih, A.; Ahmad, J. U.; Nieger, M.; Leskela, M.; Repo, T. Adv. Synth. Catal. 2009, 351, 2625.
												 doi: 10.1002/adsc.200900478
											
										
				Konning, D.; Hiller, W.; Christmann, M. Org. Lett. 2012, 14, 5258.
												 doi: 10.1021/ol302420k
											
										
				Hoover, J. M.; Steves, J. E.; Stahl, S. S. Nat. Protoc. 2012, 7, 1161.
												 doi: 10.1038/nprot.2012.057
											
										
				Ragagnin, G.; Betzemeier, B.; Quici, S.; Knochel, P. Tetrahedron 2002, 58, 3985.
												 doi: 10.1016/S0040-4020(02)00250-8
											
										
				Betzemeier, B. Cavazzini, M.; Quici, S.; Knochel, P. Tetrahedron Lett. 2000, 41, 4343.
												 doi: 10.1016/S0040-4039(00)00620-1
											
										
				Ansari, I. A.; Gree, R. Org. Lett. 2002, 4, 1507.
												 doi: 10.1021/ol025721c
											
										
				Liu, K. J.; Fu, Y. L.; Xie, L. Y.; Wu, C.; He, W. B.; Peng, S.; Wang, Z.; Bao, W. H.; Cao, Z.; Xu, X. H.; He, W. M. ACS Sustainable Chem. Eng. 2018, 6, 4916.
												 doi: 10.1021/acssuschemeng.7b04400
											
										
				Jiang, X. G.; Zhai, Y. Z.; Chen, J. Y.; Han, Y. L.; Yang, Z.; Ma, S. M. Chin. J. Chem. 2018, 36, 15.
												 doi: 10.1002/cjoc.201700576
											
										
				Steves, J. E.; Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 15742.
												 doi: 10.1021/ja409241h
											
										
				Gamez, P.; Reedijk, J.; Sheldon, R. A. Chem. Commun. 2003, 2414.
										 
				Hoover, J. M.; Stahl, S. S. J. Am. Chem. Soc. 2011, 133, 16901.
												 doi: 10.1021/ja206230h
											
										
				Kumpulainen, E. T. T.; Koskinen, A. M. P. Chem.-Eur. J. 2009, 15, 10901.
												 doi: 10.1002/chem.200901245
											
										
				Steves, J. E.; Stahl, S. S. J. Org. Chem. 2015, 80, 11184.
												 doi: 10.1021/acs.joc.5b01950
											
										
				Hill, N. J.; Hoover, J. M.; Stahl, S. S. J. Chem. Educ. 2013, 90, 102.
												 doi: 10.1021/ed300368q
											
										
				Hoover, J. M.; Ryland, B. L.; Stahl, S. S. ACS Catal. 2013, 3, 2599.
												 doi: 10.1021/cs400689a
											
										
				Corre, Y.; Rysak, V.; Capet, F.; Djukic, J. P.; Agbossou-Niedercorn, F.; Michon, C. Chemistry 2016, 22, 14036.
												 doi: 10.1002/chem.201602867
											
										
				Zhan, L. W.; Han, L.; Xing, P.; Jiang, B. Chemistry 2016, 47, 5990.
										 
 
						
						
						
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