Abstract
Methyl esters can be produced in high yields by oxiding methanolic solutions of primary alcohols with dioxygen over a heterogeneous gold catalyst. The versatility of this new methodology is demonstrated by the fact that alkylic, benzylic and allylic alcohols, as well as alcohols containing an amine functionality are oxidized in good to excellent yields.
Similar content being viewed by others
References
ten Brink G.-J., Arends I.W.C.E., Sheldon R.A. (2000) Science 287:1636
Mori K., Hara T., Mizugaki T., Ebitani K., Kaneda K. (2004) J. Am Chem. Soc. 126:10657
Ebitani K., Motokura K., Muzugaki K., Kaneda K. (2005) Angew. Chem Int. Ed. 44:3423
Mallat T., Baiker A. (2004) Chem. Rev. 104:3037
Hutchings G.J., Haruta M. (2005) Appl. Catal. A. 291:2
Hutchings G.J. (2005) Catal. Today 100:55
Bond G.C., Louis C., Thompson D.T. (2006) Catalysis by Gold. Imperial College Press, London
Thompson D.T. (2006) Top. Catal. 38:231
Haruta M., Kobayashi T., Sano H., Yamada N. (1987) Chem. Lett. 4:405
Haruta M., Yamada N., Kobayashi T., Iilima S. (1989) J. Catal. 115:301
Hutchings G.J. (1985) J. Catal. 96:292
Prati L., Rossi M. (1998) J. Catal. 176:552
Bianchi C., Porta F., Prati L., Rossi M. (2000) Top. Catal. 13:231
S. Carrettin, P.McMorn, P. Johnston, K. Griffin, G.J Hutchings, Chem. Commun. (2002) 696
Abad A., Almela C., Corma A., Garcia H. (2006) Tetrahedron 62 :6666
Enache D.I., Knight D.W., Hutchings G.J. (2005) Catal. Lett. 103:43
Christensen C.H., Jørgensen B., Rass-Hansen J., Egeblad K., Madsen R., Klitgaard S.K., Hansen S.M., Hansen M.R., Andersen H.C., Riisager A. (2006) Angew. Chem. Int. Ed. 45:4648
Lopez N., Nørskov J.K. (2002) J. Am. Chem. Soc. 124:11262
Valden M., Lai X., Goodmann D.W. (1998) Science 281:1647
Mori N., Togo H. (2005) Tetrahedron 61:5915
Hiegel G.A., Gilley C.B. (2003) Synth. Commun. 33:2003
Karade N.N., Huple D.B. (2005) Synlett 13:2039
Milocanovic J.N., Vasojevic M., Gojkovic S. (1991) J. Chem. Soc., Perkin Trans. 2:1231
McDonald C.E., Nice L.E., Nestor N.B. (1993) Tetrahedron Lett. 34:2744
Y. Hiroshi, K. Ariyoshi, T. Hayashi, PCT Int. Patent Appl. WO 2004050600 (2004)
Hayashi T., Inagaki T., Itayama N., Baba H. (2006) Catal. Today 117:210
Acknowledgments
The Center for Sustainable and Green Chemistry is sponsored by the Danish National Research Foundation.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Nielsen, I.S., Taarning, E., Egeblad, K. et al. Direct aerobic oxidation of primary alcohols to methyl esters catalyzed by a heterogeneous gold catalyst. Catal Lett 116, 35–40 (2007). https://doi.org/10.1007/s10562-007-9086-9
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-007-9086-9