Abstract
Copper(II) on 4-Å molecular sieves is an efficient catalyst for the preparation of imines from benzylamines under simple reaction conditions. No oxidative atmosphere or oxidizing agents are required. Preparative experiments showed that no aldehyde intermediate can be detected even under ambient atmospheric conditions.
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Adams JP (2000) J Chem Soc Perkin Trans 1:125
Kobayashi S, Mori Y, Fossey JS, Salter MM (2011) Chem Rev 111:2626
Schiff H (1864) Justus Liebigs Ann Chem 131:118
Sprung MM (1940) Chem Rev 26:297
Layer RW (1963) Chem Rev 63:489
Qin W, Long S, Panunzio M, Biondi S (2013) Molecules 18:12264
Angelici RJ (2013) Catal Sci Technol 3:279
Largeron M (2013) Eur J Org Chem 5225
Patil RD, Adimurthy S (2011) Adv Synth Catal 353:1695
Huang B, Tian H, Lin S, Xie M, Yu X, Xu Q (2013) Tetrahedron Lett 54:2861
Hu Z, Kerton FM (2012) Org Biomol Chem 10:1618
Prades A, Peris E, Albrecht M (2011) Organometallics 30:1162
He LP, Chen T, Gong D, Lai Z, Huang KW (2012) Organometallics 31:5208
Zhu B, Angelici RJ (2007) Chem Commun 2157
Zhu B, Lazar M, Trewyn BG, Angelici RJ (2008) J Catal 260:1
Aschwanden L, Panella B, Rossbach P, Keller B, Baiker A (2009) ChemCatChem 1:111
Cuia W, Xiaoc Q, Sarinac S, Aoa W, Xied M, Zhuc H, Baoa Z (2014) Catal Today 235:152
Khusnutdinov RI, Baygusina AR, Aminov RI (2012) Russian J Org Chem 48:1059
Zhao S, Liu C, Guo Y, Xiao JC, Chen QY (2014) J Org Chem 79:8926
Nakayama K, Hamamot M, Nishiyama Y, Ishii Y (1993) Chem Lett 22:1699
Kodama S, Yoshida J, Nomoto A, Ueta Y, Yano S, Ueshima M, Ogawa A (2010) Tetrahedron Lett 51:2450
Chu G, Li C (2010) Org Biomol Chem 8:4716
Liu L, Wang Z, Fu X, Yan CH (2012) Org Lett 14:5692
Lang X, Ma W, Zhao Y, Chen C, Ji H, Zhao J (2012) Chem Eur J 18:2624
Lang X, Ji H, Chen C, Ma W, Zhao J (2011) Angew Chem Int Ed 50:3934
Lang X, Ma W, Chen C, Ji H, Zhao J (2014) Acc Chem Res 47:355
Wendlandt AE, Stahl SS (2012) Org Lett 14:2850
Lang X, Chen X, Zhao J (2014) Chem Soc Rev 43:473
Atanassova V, Ganno K, Kulkarni A, Landge SM, Curtis S, Foster M, Török B (2011) Appl Clay Sci 53:220
Landge SM, Atanassova V, Thimmaiahb M, Török B (2007) Tetrahedron Lett 48:5161
Tayade KN, Mishra MJ (2014) Mol Cat A Chem 382:114
Fodor A, Kiss Á, Debreczeni N, Hell Z, Gresits I (2010) Org Biomol Chem 8:4575
Németh J, Debreczeni N, Gresits I, Bálint M, Hell Z (2015) Cat Lett 145:1113
Hegedűs A, Hell Z, Potor A (2006) Synth Commun 36:3625
Kwon MS, Kim S, Park S, Bosco W, Chidrala RK, Park J (2009) J Org Chem 74:2877
Saha B, Wahidur Rahaman SM, Daw P, Sengupta G, Bera JK (2014) Chem Eur J 20:6542
Youn SW (2006) J Org Chem 71:2521
Gnanaprakasam B, Zhang J, Milsten D (2010) Angew Chem Int Ed 49:1468
Decker H, Becker P (1913) Liebigs Ann 395:62
Sekiya M, Morimoto T (1975) Chem Pharm Bull 23:2353
Hayashi H, Ohno A, Oka S (1975) Bull Inst Chem Res Kyoto Univ 53:489
Acknowledgments
Á. M. is grateful to Chinoin Pharmaceuticals Ltd. for the financial support. This work was financially supported by the New Széchenyi Development Plan (TÁMOP-4.2.1/B-09/1/KMR-2010-0002).
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Magyar, Á., Hell, Z. Heterogeneous copper-catalyzed coupling of amines: a possible way for the preparation of imines. Monatsh Chem 147, 1583–1589 (2016). https://doi.org/10.1007/s00706-016-1784-9
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DOI: https://doi.org/10.1007/s00706-016-1784-9