N-alkylation of ethylenediamine with alcohols catalyzed by CuO-NiO/γ-Al2O3

[1] Balcells, D., Nova, A., Clot, E., Gnanamgari, D., Crabtree, R. H., & Eisenstein, O. (2008). Mechanism of homogeneous iridium-catalyzed alkylation of amines with alcohols from a DFT study. Organometallics, 27, 2529–2535. DOI: 10.1021/om800134d. http://dx.doi.org/10.1021/om800134d10.1021/om800134dSearch in Google Scholar

[2] Bernady, K. F. (1979). U.S. Patent No. 7,849,118. Washington, DC, USA: U.S. Patent and Trademark Office. Search in Google Scholar

[3] Chen, H., Zhang, T., Qian, C., & Chen, X. (2010). A novel method for N-alkylation of aliphatic amines with ethers over γ-Al2O3. Chemical Papers, 64, 537–540. DOI: 10.2478/s11696-010-0033-7. http://dx.doi.org/10.2478/s11696-010-0033-710.2478/s11696-010-0033-7Search in Google Scholar

[4] Dobereiner, G. E., & Crabtree, R. H. (2010). Dehydrogenation as a substrate-activating strategy in homogeneous transitionmetal catalysis. Chemical Reviews, 110, 681–703. DOI: 10.1021/cr900202j. http://dx.doi.org/10.1021/cr900202j10.1021/cr900202jSearch in Google Scholar

[5] Fujita, K. I., Li, Z., Ozeki, N., & Yamaguchi, R. (2003). N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex. Tetrahedron Letters, 44, 2687–2690. DOI: 10.1016/s0040-4039(03)00371-x. http://dx.doi.org/10.1016/S0040-4039(03)00371-X10.1016/S0040-4039(03)00371-XSearch in Google Scholar

[6] Grigg, R., Mitchell, T. R. B., Sutthivaiyakit, S., & Tongpenyai, N. (1981). Transition metal-catalysed N-alkylation of amines by alcohols. Journal of Chemical Society, Chemical Communications, 12, 611–612. DOI: 10.1039/c39810000611. http://dx.doi.org/10.1039/c3981000061110.1039/c39810000611Search in Google Scholar

[7] Guillena, G., Ramón, D. J., & Yus, M. (2010). Hydrogen autotransfer in the N-alkylation of amines and related compounds using alcohols and amines as electrophiles. Chemical Reviews, 110, 1611–1641. DOI: 10.1021/cr9002159. http://dx.doi.org/10.1021/cr900215910.1021/cr9002159Search in Google Scholar PubMed

[8] Guérin, C., Bellosta, V., Guillamot, G., & Cossy, J. (2011). Mild nonepimerizing N-alkylation of amines by alcohols without transition metals. Organic Letters, 13, 3534–3537. DOI: 10.1021/ol201351a. http://dx.doi.org/10.1021/ol201351a10.1021/ol201351aSearch in Google Scholar PubMed

[9] Hamid, M. H. S. A., Slatford, P. A., & Williams, J. M. J. (2007). Borrowing hydrogen in the activation of alcohols. Advanced Synthesis & Catalysis, 349, 1555–1575. DOI: 10.1002/adsc.200600638. http://dx.doi.org/10.1002/adsc.20060063810.1002/adsc.200600638Search in Google Scholar

[10] Hamid, M. H. S. A., & Williams, J. M. J. (2007). Ruthenium catalysed N-alkylation of amines with alcohols. Chemical Communications, 7, 725–727. DOI: 10.1039/b616859k. http://dx.doi.org/10.1039/b616859k10.1039/b616859kSearch in Google Scholar PubMed

[11] He, J. L., Yamaguchi, K., & Mizuno, N. (2010). Selective synthesis of secondary amines via N-alkylation of primary amines and ammonia with alcohols by supported copper hydroxide catalysts. Chemistry Letters, 39, 1182–1183. DOI: 10.1246/cl.2010.1182. http://dx.doi.org/10.1246/cl.2010.118210.1246/cl.2010.1182Search in Google Scholar

[12] Kim, J. W., Yamaguchi, K., & Mizuno, N. (2009). Heterogeneously catalyzed selective N-alkylation of aromatic and heteroaromatic amines with alcohols by a supported ruthenium hydroxide. Journal of Catalysis, 263, 205–208. DOI: 10.1016/j.jcat.2009.01.020. http://dx.doi.org/10.1016/j.jcat.2009.01.02010.1016/j.jcat.2009.01.020Search in Google Scholar

[13] Lawrence, S. A. (2004). Amines: Synthesis, properties and applications. Cambridge, UK: Cambridge University Press. Search in Google Scholar

[14] Martínez-Asencio, A. M., Ramón, D. J., & Yus, M. (2010). N-alkylation of poor nucleophilic amine and sulfonamide derivatives with alcohols by a hydrogen autotransfer process catalyzed by copper(II) acetate. Tetrahedron Letters, 51, 325–327. DOI: 10.1016/j.tetlet.2009.11.009. http://dx.doi.org/10.1016/j.tetlet.2009.11.00910.1016/j.tetlet.2009.11.009Search in Google Scholar

[15] Saidi, O., Blacker, A. J., Lamb, G. W., Marsden, S. P., Taylor, J. E., & Williams, J. M. J. (2010). Borrowing hydrogen in water and ionic liquids: iridium-catalyzed alkylation of amines with alcohols. Organic Process Research & Development, 14, 1046–1049. DOI: 10.1021/op100024j. http://dx.doi.org/10.1021/op100024j10.1021/op100024jSearch in Google Scholar

[16] Salvatore, R. N., Schmidt, S. E., Shin, S., Nagle, A. S., Worrell, J. H., & Jung, K. W. (2000). CsOH-promoted chemoselective mono-N-alkylation of diamines and polyamines. Tetrahedron Letters, 41, 9705–9708. DOI: 10.1016/s0040-4039(00)01747-0. http://dx.doi.org/10.1016/S0040-4039(00)01747-010.1016/S0040-4039(00)01747-0Search in Google Scholar

[17] Takeuchi, R., Tsuji, Y., & Watanabe, Y. (1986). Platinum complex-catalysed carbonylations of organic iodides having β-hydrogens attached to sp3-carbons. Journal of Chemical Society, Chemical Communications, 4, 351–352. DOI: 10.1039/c39860000351. http://dx.doi.org/10.1039/c3986000035110.1039/C39860000351Search in Google Scholar

[18] Valot, F., Fache, F., Jacquot, R., Spagnol, M., & Lemaire, M. (1999). Gas-phase selective N-alkylation of amines with alcohols over γ-alumina. Tetrahedron Letters, 40, 3689–3692. DOI: 10.1016/s0040-4039(99)00588-2. http://dx.doi.org/10.1016/S0040-4039(99)00588-210.1016/S0040-4039(99)00588-2Search in Google Scholar

[19] Yamakawa, T., Tsuchiya, I., Mitsuzuka, D., & Ogawa, T. (2004). Alkylation of ethylenediamine with alcohols by use of Cu-based catalysts in the liquid phase. Catalysis Communications, 5, 291–295. DOI: 10.1016/j.catcom.2004.03.004. http://dx.doi.org/10.1016/j.catcom.2004.03.00410.1016/j.catcom.2004.03.004Search in Google Scholar