One-Pot Synthesis of Menthol Catalyzed by a Highly Diastereoselective Au/MgF2 Catalyst†
Dipl.-Chem. Alina Negoi
Department Of Chemical Technology and Catalysis, Faculty of Chemistry, University of Bucharest, Bdul Regina Elisabeta 4-12, 030016 Bucharest (Romania), Fax: (+40) 214-100-241
Search for more papers by this authorDr. Stefan Wuttke
Institut fur Chemie, Humboldt-Universitat zu Berlin, Brook-Taylor-Strasse 2, 12489 Berlin (Germany), Fax: (+49) 30-2093-7468
Search for more papers by this authorProf. Dr. Erhard Kemnitz
Institut fur Chemie, Humboldt-Universitat zu Berlin, Brook-Taylor-Strasse 2, 12489 Berlin (Germany), Fax: (+49) 30-2093-7468
Search for more papers by this authorDr. Dan Macovei
National Institute of Materials Physics, Bucharest (Romania)
Search for more papers by this authorProf. Dr. Vasile I. Parvulescu
Department Of Chemical Technology and Catalysis, Faculty of Chemistry, University of Bucharest, Bdul Regina Elisabeta 4-12, 030016 Bucharest (Romania), Fax: (+40) 214-100-241
Search for more papers by this authorDr. C. M. Teodorescu
National Institute of Materials Physics, Bucharest (Romania)
Search for more papers by this authorProf. Dr. Simona M. Coman
Department Of Chemical Technology and Catalysis, Faculty of Chemistry, University of Bucharest, Bdul Regina Elisabeta 4-12, 030016 Bucharest (Romania), Fax: (+40) 214-100-241
Search for more papers by this authorDipl.-Chem. Alina Negoi
Department Of Chemical Technology and Catalysis, Faculty of Chemistry, University of Bucharest, Bdul Regina Elisabeta 4-12, 030016 Bucharest (Romania), Fax: (+40) 214-100-241
Search for more papers by this authorDr. Stefan Wuttke
Institut fur Chemie, Humboldt-Universitat zu Berlin, Brook-Taylor-Strasse 2, 12489 Berlin (Germany), Fax: (+49) 30-2093-7468
Search for more papers by this authorProf. Dr. Erhard Kemnitz
Institut fur Chemie, Humboldt-Universitat zu Berlin, Brook-Taylor-Strasse 2, 12489 Berlin (Germany), Fax: (+49) 30-2093-7468
Search for more papers by this authorDr. Dan Macovei
National Institute of Materials Physics, Bucharest (Romania)
Search for more papers by this authorProf. Dr. Vasile I. Parvulescu
Department Of Chemical Technology and Catalysis, Faculty of Chemistry, University of Bucharest, Bdul Regina Elisabeta 4-12, 030016 Bucharest (Romania), Fax: (+40) 214-100-241
Search for more papers by this authorDr. C. M. Teodorescu
National Institute of Materials Physics, Bucharest (Romania)
Search for more papers by this authorProf. Dr. Simona M. Coman
Department Of Chemical Technology and Catalysis, Faculty of Chemistry, University of Bucharest, Bdul Regina Elisabeta 4-12, 030016 Bucharest (Romania), Fax: (+40) 214-100-241
Search for more papers by this authorThe authors thank the CNCSIS (PNCDI II 40/2007) for financial support.
Graphical Abstract
No toxic compounds such as KCN and no thermal activation is required for the preparation of Au/MgF2 complexes by a simple and facile “incipient wetness impregnation” method in which hydrogen tetrachloroaurate (HAuCl4) is the gold precursor. One of the complexes prepared exhibits unique catalytic properties and serves as a heterogeneous catalyst for the highly diastereoselective one-pot synthesis of (±)-menthol from citronellal (see picture).
Supporting Information
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References
- 1G. C. Bond, D. T. Thompson, Catal. Rev. Sci. Eng. 1999, 41, 319–388.
- 2F. Z. Su, Y. M. Liu, L. C. Wang, Y. Cao, H. Y. He, K. N. Fan, Angew. Chem. 2008, 120, 340–343; Angew. Chem. Int. Ed. 2008, 47, 334–337.
- 3M. Valden, X. Lai, D. W. Goodman, Science 1998, 281, 1647–1650.
- 4A. Grirrane, A. Corma, H. Garcia, Science 2008, 322, 1661–1664.
- 5A. Wolf, F. Schüth, Appl. Catal. A 2002, 226, 1–13.
- 6M. D. Hughes, Y.-J. Xu, P. Jenkins, P. McMorn, P. Landon, D. I. Enache, A. F. Carley, G. A. Attard, G. J. Hutchings, F. King, E. H. Stitt, P. Johnston, K. Griffin, C. J. Kiely, Nature 2005, 437, 1132–1135.
- 7S. Biella, L. Prati, M. Rossi, J. Catal. 2002, 206, 242–247.
- 8X. Zhang, H. Shi, B.-Q. Xu, Angew. Chem. 2005, 117, 7294–7297; Angew. Chem. Int. Ed. 2005, 44, 7132–7135.
- 9S. Carrettin, J. Guzman, A. Corma, Angew. Chem. 2005, 117, 2282–2285;
10.1002/ange.200462560 Google ScholarAngew. Chem. Int. Ed. 2005, 44, 2242–2245.
- 10C. Raptis, H. Garcia, M. Stratakis, Angew. Chem. 2009, 121, 3179–3182;
10.1002/ange.200805838 Google ScholarAngew. Chem. Int. Ed. 2009, 48, 3133–3136.
- 11S. Wuttke, S. M. Coman, G. Scholz, H. Kirmse, A. Vimont, M. Daturi, S. L. M. Schroeder, E. Kemnitz, Chem. Eur. J. 2008, 14, 11488–11499.
- 12S. M. Coman, P. Patil, S. Wuttke, E. Kemnitz, Chem. Commun. 2009, 460–462.
- 13S. M. Coman, V. I. Parvulescu, S. Wuttke, E. Kemnitz, ChemCatChem 2010, 2, 92–97.
- 14Y. Nakatani, K. Kawashima, Synthesis 1978, 147–148.
- 15C. Milone, A. Parri, A. Pistone, G. Neri, S. Galvagno, Appl. Catal. A 2002, 233, 151–157.
- 16K. Arata, C. Matsuura, Chem. Lett. 1989, 1797–1798.
- 17F. Neaţu, S. Coman, V. I. Pârvulescu, G. Poncelet, D. de Vos, P. A. Jacobs, Top. Catal. 2009, 52, 1292–1300.
- 18A. Corma, M. Renz, Chem. Commun. 2004, 550–551.
- 19Z. Yongzhong, N. Yuntong, S. Jaenicke, G. K. Chuah, J. Catal. 2005, 229, 404–413.
- 20S. Wuttke, S. M. Coman, J. Kröhnert, F. C. Jentoft, E. Kemnitz, Catal. Today 2010, 152, 2–10.
- 21D. E. O’Reilly, E. M. Peterson, C. E. Scheie, J. M. Williams, J. Chem. Phys. 1971, 55, 5629–5635.
- 22R. B. Greegor, F. W. Lytle, J. Catal. 1980, 63, 476–486.
- 23H. H. Kung, M. C. Kung, C. K. Costello, J. Catal. 2003, 216, 425–432.
- 24B. Hammer, J. K. Nørskov, Nature 1995, 376, 238–240.
- 25K. H. Schulte-Elte, G. Ohloff, Helv. Chim. Acta 1967, 50, 153–165.
- 26F. Neaţu, Z. Li, R. Richards, P. Y. Toullec, J.-P. Genêt, K. Dumbuya, J. M. Gottfried, H.-P. Steinrück, V. I. Pârvulescu, V. Michelet, Chem. Eur. J. 2008, 14, 9412–9418.
- 27G. K. Chuah, S. H. Liu, S. Jaenicke, L. J. Harrison, J. Catal. 2001, 200, 352–359.
- 28A. Comas-Vives, C. Gonzalez-Arellano, A. Corma, M. Iglesias, F. Sanchez, G. Ujaque, J. Am. Chem. Soc. 2006, 128, 4756–4765.
- 29S. Rüdiger, U. Groß, E. Kemnitz, J. Fluorine Chem. 2007, 128, 353–368.
- 30S. M. Coman, S. Wuttke, A. Vimont, M. Daturi, E. Kemnitz, Adv. Synth. Catal. 2008, 350, 2517–2524.
