摘要
以Fe-MIL-101为非均相催化剂,通过多种伯胺与2,5-二甲氧基四氢呋喃进行Paal-Knorr反应,高效合成相应的吡咯衍生物.在Fe-MIL-101结构中,裸露的Fe(Ⅲ)配位点作为催化活性中心参与吡咯衍生物的催化合成反应.同时Fe-MIL-101的高比表面积和大的孔尺寸确保了底物分子与催化活性中心的充分接触以及产物的自由脱离,从而促进了催化反应的快速进行.Fe-MIL-101在催化反应过程中具有很好的稳定性,多次循环使用后仍能表现出良好的催化性能.此外,该催化剂在伯胺(包括脂肪胺、芳香胺)与2,5-己二酮的Paal-Knorr缩合反应中也具有优异的催化性能.
A highly porous metal-organic frameworks( Fe-MIL-101) was synthesized as a heterogeneous catalyst for the Paal-Knorr reaction. The free coordination position of Fe( Ⅲ) in Fe-MIL-101 can be used as catalytic active sites for the Paal-Knorr reaction. The large surface area and pore size of Fe-MIL-101 contribute to offer an access for organic substrates to the active sites sufficiently, which ensure a high catalytic performance of Fe-MIL-101 for pyrroles. The catalyst could be reused five times without loss of its catalytic activity. In addition,the catalyst also exhibits high catalytic activity in other amines system with 2,5-hexanedione for Paal-Knorr condensation reaction.
引文
[1]Adhikari A.,Radhakrishnan S.,Vijayan M.,J.Appl.Polym.Sci.,2012,125,1875—1881
[2]Andersen R.J.,Faulkner D.J.,Cun-heng H.,van Duyne G.D.,Clardy J.,J.Am.Chem.Soc.,1985,107(19),5492—5495
[3]Fürstner A.,Angew.Chem.Int.Ed.,2003,42,308—311
[4]Dieter R.K.,Yu H.,Org.Lett.,2000,2,2283—2286
[5]Hantzsch A.,Dtsch Ber.,Chem.Ges.,1890,23,1474—1476
[6]Ferreira V.F.,de Souza M.C.B.V.,Cunha A.C.,Pereira L.O.R.,Ferreira M.L.G.,Org.Prep.Proced.Int.,2001,33,411—454
[7]Berree F.,Marchand E.,Morel G.,Tetrahedron Lett.,1992,33,6155—6158
[8]Lee C.F.,Yang I.M.,Hwu T.Y.,Feng A.S.,Tseng J.C.,Luh T.Y.,J.Am.Chem.Soc.,2000,122,4992—4993
[9]Chiu P.K.,Sammes M.P.,Tetrahedron,1990,46,3439—3456
[10]Wang B.,Gu Y.,Luo C.,Yang T.,Yang L.,Suo J.,Tetrahedron Lett.,2004,45,3417—3419
[11]Chen J.X.,Wu H.T.,Zheng Z.G.,Jin C.,Zhang X.X.,Su W.K.,Tetrahedron Lett.,2006,47,5383—5387
[12]Luo H.T.,Kang Y.R.,Li Q.,Yang L.M.,Heteroat.Chem.,2008,19,144—148
[13]Azizi N.,Davoudpour A.,Eskandari F.,Batebi E.,Monatsh.Chem.,2013,144,405—409
[14]Monnier F.,Taillefer M.,Angew.Chem.Int.Ed.,2009,48,6954—6971
[15]Deng H.J.,Fang Y.J.,Chen G.W.,Liu M.C.,Wu H.Y.,Chen J.X.,Appl.Organomet.Chem.,2012,26,164—167
[16]Jafari A.A.,Amini S.,Tamaddon F.,J.Appl.Polym.Sci.,2012,125,1339—1345
[17]Polshettiwar V.,Varma R.S.,Tetrahedron,2010,66,1091—1097
[18]Polshettiwar V.,Baruwati B.,Varma R.S.,Chem.Commun.,2009,1837—1839
[19]Sreekumar R.,Raghavakaimal P.,Synth.Commun.,1998,28(9),1661—1665
[20]Song G.Y.,Wang B.,Wang G.,Kang Y.R.,Yang T.,Yang L.M.,Synth.Commun.,2005,35,1051—1057
[21]Xie S.M.,Zhang Z.J.,Yuan L.M.,Chem.J.Chinese Universities,2014,35(8),1652—1657(谢生明,张泽俊,袁黎明.高等学校化学学报,2014,35(8),1652—1657)
[22]Song L.F.,Zhang J.,Sun L.X.,Xu F.,Li F.,Zhang H.Z.,Si X.L.,Jiao C.L.,Li Z.B.,Liu S.,Liu Y.L.,Zhou H.Y.,Sun D.,Du Y.,Cao Z.,Gabelica Z.,Energy Environ.Sci.,2012,5,7508—7520
[23]Xu L.,Chen C.,Wang R.,Luo J.H.,Liu Y.L.,Zhang N.,Chem.J.Chinese Universities,2013,34(8),1907—1912(徐力,陈超,王瑞,罗家还,刘云凌,张宁.高等学校化学学报,2013,34(8),1907—1912)
[24]Furukawa H.,Cordova K.E.,O’Keeffe M.,Yaghi O.M.,Science,2013,341,1230444-1—12
[25]Song F.J.,Zhang T.,Wang C.,Lin W.B.,Proc.R.Soc.A.,2012,468,2035—2052
[26]Zhang Y.,Yang X.G.,Wang Q.Y.,Yao J.,Hu J.,Wang G.Y.,Chem.J.Chinese Universities,2014,35(3),613—618(张毅,杨先贵,王庆印,姚洁,胡静,王公应.高等学校化学学报,2014,35(3),613—618)
[27]O’Keeffe M.,Yaghi O.M.,Chem.Rev.,2012,112,675—702
[28]Lee J.Y.,Farha O.K.,Roberts J.,Scheidt K.A.,Nguyen S.B.T.,Hupp J.T.,Chem.Soc.Rev.,2009,38,1450—1459
[29]Tang J.,Dong W.J.,Wang G.,Yao Y.Z.,Cai L.,Liu Y.,Zhao X.,Xu J.Q.,Tan L.,RSC Adv.,2014,4,42977—42982
[30]Tang J.,Yang M.,Yang M.,Dong W.J.,Wang G.,New J.Chem.,2015,39,4919—4923
[31]Phan N.T.S.,Nguyen T.T.,Luu Q.H.,Nguyen L.T.L.,J.Mol.Catal.A:Chem.,2012,363/364,178—185
[32]Dhakshinamoorthy A.,Alvaro M.,Garcia H.,Adv.Synth.Catal.,2010,352,3022—3030
[33]Kathryn M.L.,Pashow T.,Rocca J.D.,Xie Z.G.,Tran S.,Lin W.B.,J.Am.Chem.Soc.,2009,131,14261—14263
[34]Azizi N.,Khajeh-Amiri A.,Ghafuri H.,Bolourtchian M.,Saidi M.R.,Synlett.,2009,14,2245—2248
[35]Wang F.H.,Zhu X.D.,Miao H.,J.Anhui Poly.Univ.,2014,29(2),26—30(王芬华,朱贤东,苗慧.安徽工程大学学报,2014,29(2),26—30)