七水三氯化铈-碘化钠/二氧化硅-壳聚糖催化剂的制备及其在脱保护反应中的应用
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摘要
分别以Y沸石、活性碳和二氧化硅-壳聚糖(Si O_2-CS)为载体、利用浸渍法制备了一系列负载型七水三氯化铈-碘化钠(Ce Cl_3·7H_2O-Na I)催化剂,考察了它们在叔丁基苯基醚的脱保护反应中的催化性能。结果表明,Si O_2-CS为载体的催化剂呈现出良好的催化性能和较高的稳定性。另外,在中性条件下,Si O_2-CS负载Ce Cl_3·7H_2O-Na I催化剂在叔丁基醚及1,3-二硫缩醛脱保护反应中呈现出较高的催化活性,从而避免使用强酸和强碱。
A series of Ce Cl_3·7H_2O/Na I catalysts immobilized on various supports such as Y zeolite,activated carbon,and Si O_2-CS was prepared. Their catalytic performances were evaluated in the deprotection reactions of tert-butyl phenyl ether. The supported catalyst exhibits good stability and catalytic activity. To further investigate the application of Si O_2-CS-Ce Cl_3·7H_2O/Na I system in other deprotection reactions,t-butyl ether and 1,3-dithioacetals were explored. In neutral conditions, the catalyst can effectively promote the deprotection reaction,and the use of strong acid and strong base can be avoided.
A series of Ce Cl_3·7H_2O/Na I catalysts immobilized on various supports such as Y zeolite,activated carbon,and Si O_2-CS was prepared. Their catalytic performances were evaluated in the deprotection reactions of tert-butyl phenyl ether. The supported catalyst exhibits good stability and catalytic activity. To further investigate the application of Si O_2-CS-Ce Cl_3·7H_2O/Na I system in other deprotection reactions,t-butyl ether and 1,3-dithioacetals were explored. In neutral conditions, the catalyst can effectively promote the deprotection reaction,and the use of strong acid and strong base can be avoided.
引文
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[18]Baig R B N,Varma R S.Magnetic Silica Supported Copper:A Modular Approach to Aqueous Ullmann-Type Amination of Aryl Halides[J].RSC Adv,2014,4(13):6568-6572.
[19]WU Chun,DAI Lijun,LIU Tao.Catalytic Properties of Silica-Supported Chitosan-Pd(Ⅱ)in Coupling Reation of Organotins and Acid Chlorides[J].Ind Catal,2005,13(2):36-38(in Chinese).吴春,代丽君,刘涛.Si O2负载壳聚糖和钯对三丁基烃基锡与酰氯偶联反应的催化活性[J].工业催化,2005,13(2):36-38.
[20]Gadwal I,Khan A.Multiply Functionalized Dendrimers:Protective-group-free Synthesis Through Sequential Thiolepoxy‘click’Chemistry and Esterification Reaction[J].RSC Adv,2015,5(55):43961-43964.
[21]Bhatt M V,Kulkarni S U.Cleavage of Ethers[J].Synthesis,1983,1983(4):249-282.
[22]Bartoli G,Bosco M,Carlone A,et al.tert-Butyl Ethers:Renaissance of An Alcohol Protecting Group.Facile Cleavage with Cerium(Ⅲ)Chloride/Sodium Iodide[J].Adv Synth Catal,2006,348(7/8):905-910.
[23]Yadav J S,Reddy B V S,Raghavendra S,et al.Ce Cl37H2O-Promoted Highly Chemoselective Hydrolysis of 1,3-Oxathioand Dithioacetals[J].Tetrahedron Lett,2002,43(26):4679-4681.
[2]ZHANG Xiongwei,CHU Wei,WANG Xiaodong,et al.Preparation of Alumina-Supported Nobel Metal Iridium Catalysts and Their Catalytic Performance for Methanol Decomposition[J].Chinese J Catal,2006,27(10):863-867(in Chinese).张雄伟,储伟,王晓东,等.氧化铝担载的贵金属铱基催化剂的制备及其对甲醇裂解反应的催化性能[J].催化学报,2006,27(10):863-867.
[3]Xue W,Zhang J,Wang Y,et al.Effect of Promoter Copper on the Oxidative Carbonylation of Phenol over the Ultrafine Embedded Catalyst Pd-Cu-O/Si O2[J].J Mol Catal A:Chem,2005,232(1/2):77-81.
[4]LIU Yingxin,LI Qiugui,YAN Wei.Co/Ti O2-Si O2Selective Hydrogenation of Cinnamaldehyde to Cinnamyl Alcohol over Co/Ti O2-Si O2Catalysts[J].J Chem Ind Eng,2009,60(1):98-103(in Chinese).刘迎新,李秋贵,严巍.Co/Ti O2-Si O2催化剂上肉桂醛选择性加氢制备肉桂醇[J].化工学报,2009,60(1):98-103.
[5]ZHANG Fumin,YUAN Chaoshu,WANG Jun.Catalytic Performance of Phosphotungstic Acid(Salt)Supported on Si O2for Acetalization of Ethyl Acetoacetate with Glycol[J].Petrochem Technol,2005,34(12):1172-1176(in Chinese).张富民,袁超树,王军.Si O2负载磷钨酸(盐)催化剂对乙酰乙酸乙酯与乙二醇缩合反应的催化性能[J].石油化工,2005,34(12):1172-1176.
[6]PENG Qingrong,HOU Shicong,ZHANG Chunrong,et al.Catalytic Properties of Ultrafine Si O2Supported Amphiphilic Phosphine-Rh Complex Catalysts[J].J Petrochem Univ,2010,23(1):19-22(in Chinese).彭庆蓉,侯士聪,张春荣,等.超细Si O2负载型两亲性铑膦络合物催化性能研究[J].石油化工高等学校学报,2010,23(1):19-22.
[7]Kim W B,Park E D,Lee J S.Effects of Inorganic Co-Catalysts and Initial States of Pd on the Oxidative Carbonylation of Phenols over Heterogeneous Pd/C[J].Appl Catal A:Gen,2003,242(2):335-345.
[8]TAN Jun,FAN Hong,BU Zhiyang,et al.Activated Carbon Supported Al Cl3Solid Acid Catalyst:Structural Characterization and Catalytic Properties for Redistribution Reaction of Methylchloro Silane[J].J Chem Ind Eng,2006,57(12):2867-2870(in Chinese).谭军,范宏,卜志扬,等.活性炭负载Al Cl3固体酸催化甲基氯硅烷再分配反应性能与结构研究[J].化工学报,2006,57(12):2867-2870.
[9]Chou B,Tsai J L,Cheng S.Cu-Substituted Molecular Sieves as Liquid Phase Oxidation Catalysts[J].Micropor Mesopor Mater,2001,48(1/2/3):309-317.
[10]Hussain M,Song S K,Lee J H,et al.Characteristics of Como Catalysts Supported on Modified Mcm-41 and Mcm-48Materials for Thiophene Hydrodesulfurization[J].Ind Eng Chem Res,2006,45(2):536-543.
[11]Conley M P,Delley M F,Siddiqi G.Polymerization of Ethylene by Silica-Supported Dinuclear Cr III Sites Through an Initiation Step Involving C—H Bond Activation[J].Angew Chem Int Ed,2014,53(7):1872-1876.
[12]WANG Yanping,HUANG Xin,LIAO Xuepin,et al.Preparation of Palladium(0)Catalyst Supported by Silica Beads Grafted with Black-wattle Tannin and Its Properties[J].Chem Ind Eng Prog,2010,29(1):62-66(in Chinese).王艳平,黄鑫,廖学品,等.二氧化硅接枝黑荆树单宁负载钯催化剂的制备及其性能[J].化工进展,2010,29(1):62-66.
[13]Astruc D,Chardac F.Dendritic Catalysts and Dendrimers in Catalysis[J].Chem Rev,2001,101(9):2991-3024.
[14]Van Heerbeek R,Kamer P C J,Van Leeuwe P W N M,et al.Dendrimers as Support for Recoverable Catalysts and Reagents[J].Chem Rev,2002,102(10):3717-3756.
[15]Wang Z,Chen G,Ding K.Self-Supported Catalysts[J].Chem Rev,2008,109(2):322-359.
[16]Monge-Marcet A,Cattoen X,Alonso D A,et al.Recyclable Silica-Supported Prolinamide Organocatalysts for Direct Asymmetric Aldol Reaction in Water[J].Green Chem,2012,14(6):1601-1610.
[17]Laurent S,Forge D,Port M,et al.Magnetic Iron Oxide Nanoparticles:Synthesis,Stabilization,Vectorization,Physicochemical Characterizations,and Biological Applications[J].Chem Rev,2008,108(6):2064-2110.
[18]Baig R B N,Varma R S.Magnetic Silica Supported Copper:A Modular Approach to Aqueous Ullmann-Type Amination of Aryl Halides[J].RSC Adv,2014,4(13):6568-6572.
[19]WU Chun,DAI Lijun,LIU Tao.Catalytic Properties of Silica-Supported Chitosan-Pd(Ⅱ)in Coupling Reation of Organotins and Acid Chlorides[J].Ind Catal,2005,13(2):36-38(in Chinese).吴春,代丽君,刘涛.Si O2负载壳聚糖和钯对三丁基烃基锡与酰氯偶联反应的催化活性[J].工业催化,2005,13(2):36-38.
[20]Gadwal I,Khan A.Multiply Functionalized Dendrimers:Protective-group-free Synthesis Through Sequential Thiolepoxy‘click’Chemistry and Esterification Reaction[J].RSC Adv,2015,5(55):43961-43964.
[21]Bhatt M V,Kulkarni S U.Cleavage of Ethers[J].Synthesis,1983,1983(4):249-282.
[22]Bartoli G,Bosco M,Carlone A,et al.tert-Butyl Ethers:Renaissance of An Alcohol Protecting Group.Facile Cleavage with Cerium(Ⅲ)Chloride/Sodium Iodide[J].Adv Synth Catal,2006,348(7/8):905-910.
[23]Yadav J S,Reddy B V S,Raghavendra S,et al.Ce Cl37H2O-Promoted Highly Chemoselective Hydrolysis of 1,3-Oxathioand Dithioacetals[J].Tetrahedron Lett,2002,43(26):4679-4681.