Michael Addition Reaction of Malononitrile and α,β-Unsaturated Ketones Catalyzed by Amine Functionalized MCM-41

doi:10.6023/cjoc201305016

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (11): 2391-2395.DOI: 10.6023/cjoc201305016 Previous Articles Next Articles

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氨功能化的MCM-41催化丙二腈与α,β-不饱和酮的Michael加成

王长春, 谢绍雷, 解正峰, 惠永海

石油天然气精细化工教育部 & 新疆维吾尔自治区重点实验室新疆大学化学化工学院乌鲁木齐 830046

收稿日期:2013-05-10 修回日期:2013-06-13 发布日期:2013-07-10
通讯作者: 惠永海 E-mail:hyhmsq@gmail.com
基金资助:
国家自然科学基金（Nos. 21162026，20962018，20862015）资助项目.

Michael Addition Reaction of Malononitrile and α,β-Unsaturated Ketones Catalyzed by Amine Functionalized MCM-41

Wang Changchun, Xie Shaolei, Xie Zhengfeng, Hui Yonghai

Key Laboratory of Oil & Gas Fine Chemicals, Ministry of Education & Xinjiang Uyghur Autonomous Region, College of Chemistry and Chemical Engineering, Xinjiang University, Urumqi 830046

Received:2013-05-10 Revised:2013-06-13 Published:2013-07-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21162026, 20962018, 20862015).

Michael addition reaction of α, β-unsaturated ketones and malononitrile that catalyzed by amine functionalized MCM-41 in methanol afforded a series of cyano derivatives with high yield (up to 99%). The products were afforded at room temperature. Moreover, the catalyst was also found to easiness to handle up, friendly environment, and excellent recyclability.

Key words: amine functionalized MCM-41, α,β-unsaturated ketones, malononitrile, catalysis, Michael addition

Cite this article

Wang Changchun, Xie Shaolei, Xie Zhengfeng, Hui Yonghai. Michael Addition Reaction of Malononitrile and α,β-Unsaturated Ketones Catalyzed by Amine Functionalized MCM-41[J]. Chin. J. Org. Chem., 2013, 33(11): 2391-2395.

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[1] Bergmann,E.D.; Pappo,R.Org.React.Mech.1959,179.
[2] Ballini,R.; Bosica,G.; Fiorini,D.; Palmieri,A.; Petrini,M.Chem.Rev.2005,105,933.
[3] Halland,N.; Aburel,P.S.; Jorgensen,K.A.Angew.Chem.,Int.Ed.2003,115,685.
[4] Wang,J.; Li,H.; Duan,W.; Zu,L.; Wang,W.Org.Lett.2005,7,4713.
[5] Hanessian,S.; Pham,V.Org.Lett.2000,2,297.
[6] Weiberth,F.J.; Hall,S.S.J.Org.Chem.1987,52,3901.
[7] Chen,Y.C.; Xue,D.; Deng,J.G.; Cui,X.; Zhu,J.; Jiang,Y.Z.Tetrahedron Lett.2004,45,1555.
[8] Taylor,M.S.; Zalatan,D.L.; Lerchner,A.M.; Jacobsen,E.N.J.Am.Chem.Soc.2005,127,1313.
[9] Tian,J.J.; Guo,H.Y.Chin.J.Org.Chem.2012,32,193 (in Chinese).(田晶晶,郭红云,有机化学,2012,32,193.)
[10] Rong,L.C.; Han,H.X.; Jiang,H.; Zhuang,Q.Y.; Wang,S.H.; Tu,S.J.Chin.J.Org.Chem.2009,29,962 (in Chinese).(荣良策,韩红霞,姜虹,庄启亚,王苏惠,屠树江,有机化学,2009,29,962.)
[11] Ma,X.; Gang,D.R.Nat.Prod.Rep.2004,21,752.
[12] Tew,G.N.; Aamer,K.A.; Shunmugam,R.Polymer 2005,46,8440.
[13] Xie,S.L.; Hui,Y.H.; Long,X.J.; Wang,C.C.; Xie,Z.F.Chin.J.Org.Chem.2013,33,971 (in Chinese).(谢绍雷,惠永海,王长春,解正峰,有机化学,2013,33,971.)
[14] Wang,G.J.; Liu,Y.W.; Yang,Z.X.; Wang,L.; Xu,M.X.Chin.J.Org.Chem.2007,27,471 (in Chinese).(王广健,刘义武,杨振兴,王磊,徐明霞,有机化学,2007,27,471.)
[15] Parida,K.M.; Dharitri,R.J.Mol.Catal.A: Chem.2009,310,93.
[16] Hu,R.H.; Hao,W.Y.; Cai,M.Z.Chin.J.Chem.2011,29(8),1629.
[17] Mahdavinia,G.H.; Amani,A.M.; Sepehrian,H.Chin.J.Chem.2012,30,703.
[18] Chen,Y.C.; Xie,S.L.; Xie,Z.F.Chin.J.Org.Chem.2012,32,1970 (in Chinese).(陈永诚,谢绍雷,解正峰,有机化学,2012,32,1970.)
[19] Xie,S.L.; Hui,Y.H.; Long,X.J.; Wang,C.C.; Xie,Z.F.Chin.Chem.Lett.2013,24,28.
[20] Dong,X.Z.; Hui,Y.H.; Xie,S.L.; Zhang,P.; Zhou,G.P.; Xie,Z.F.RSC Adv.2013,3,3222.
[21] Zhou,G.P.; Yu,L.; Hui,Y.H.; Xie,Z.F.Acta Chim.Sinica 2012,70,1289 (in Chinese).(周广鹏,余蕾,惠永海,解正峰,化学学报,2012,70,1289.)
[22] Chen,Q.; Xin,C.; Lou,L.L.; Yu,K.; Ding,F.; Liu,S.X.Catal.Lett.2011,141,1378.
[23] Yang,W.; Jia,Y.; Du,D.M.Org.Biomol.Chem.2012,10,332.
[24] Alessio,R.; Alessandra,P.; Alessandra,L.Adv.Synth.Catal.2009,351,3067.
[25] Muthyala,M.K.; Chhikara,B.S.; Parang,K.; Kumar,A.Can.J.Chem.2012,90(3),290.
[26] Yue,L.; Du,W.; Liu,Y.K.; Chen,Y.C.Tetrahedron Lett.2008,49,3881.
[27] Li,Z.G.; Wang,Q.M.; Huang,J.M.Preparation of Organic Intermediates,2nd ed.,Chemical Industry Press,Beijing,1996,p.8 (in Chinese).(李在国,汪清民,黄君珉,有机中间体制备,第2版,化学工业出版社,北京,1996,p.8.)
[28] Oliveira,P.; Machado,A.; Ramos,A.M.; Fonseca,I.; Fernandes,F.M.B.; Botelho do Rego,A.M.; Vital,J.Microporous Mesoporous Mater.2009,120,432.

氨功能化的MCM-41催化丙二腈与α,β-不饱和酮的Michael加成

Michael Addition Reaction of Malononitrile and α,β-Unsaturated Ketones Catalyzed by Amine Functionalized MCM-41

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