Heterogenization of (η5-C5Me5)Ru(PPh3)2Cl and Its Catalytic Application for Cyclopropanation of Styrene Using Ethyl Diazoacetate

Ayyamperumal Sakthivel; Filipe E. Pedro; Anthony S. T. Chiang; Fritz E. Kühn

doi:10.1055/s-2006-926455

SPECIALTOPIC

Heterogenization of (η ⁵ -C ₅ Me ₅ )Ru(PPh ₃ ) ₂ Cl and Its Catalytic Application for Cyclopropanation of Styrene Using Ethyl Diazoacetate

Ayyamperumal Sakthivel^a, Filipe E. Pedro^a, Anthony S. T. Chiang^b, Fritz E. Kühn*^a,c
^a Lehrstuhl für Anorganische Chemie der Technischen Universität München, Lichtenbergstraße 4, 85747 Garching bei München, Germany
Fax: +49(89)28913473; e-Mail: fritz.kuehn@ch.tum.de;
^b National Central University, Chung-Li, Taiwan 320, Republic of China
^c Department of Chemistry, Instituto Tecnológico e Nuclear (ITN), Estrada Nacional 10, 2686-953 Sacavém, Portugal

Abstract

All articles of this category

Abstract

(η⁵-C₅Me₅)Ru(PPh₃)₂Cl (1) is heterogenized on the surface of mesoporous molecular sieves by direct grafting on mesoporous aluminosilicates or by reaction of an aminosilane-linker-modified silicate surface with the chloride ligand. Elemental analyses reveal that the grafted samples contain 0.2-1.8 wt% Ru. The retaining of long-range ordering of mesoporous MCM-41 and MCM-48 after grafting is evidenced from XRD, N₂ adsorption-desorption and TEM analysis. FT-IR, TG-MS, ²⁹Si and ¹H CP MAS-NMR spectra confirm the successful grafting of complex 1 on the surface of these mesoporous materials. Mesoporous materials grafted with complex 1 are found to be promising catalysts for the cyclopropanation of styrene with ethyl diazoacetate.

Key words

cyclopropanation - ethyl diazoacetate - ruthenium complex - mesoporous materials

Full Text

References

1a Baratta W. del Zotto A. Rigo P. Chem. Commun. 1997, 2163

1b Baratta W. del Zotto A. Rigo P. Organometallics 1999, 18: 5091

1c del Zotto A. Baratta W. Miani F. Verardo G. Rigo P. Eur. J. Org. Chem. 2000, 3731

1d Baratta W. Herrmann WA. Rigo P. Schwarz J. J. Organomet. Chem. 2000, 593-594: 489

1e Baratta W. del Zotto A. Herdtweck E. Vuano S. Rigo P. J. Organomet. Chem. 2001, 617: 511

1f Mayr M. Buchmeiser MR. Wurst K. Adv. Synth. Catal. 2002, 344: 712

2a Fujimura O. Honma T. Tetrahedron Lett. 1998, 39: 625

2b Schwab P. Grubbs RH. Ziller J. J. Am. Chem. Soc. 1996, 118: 100

3a Lebel H. Parquet V. Proulx C. Angew. Chem. Int. Ed. 2001, 40: 2887

3b Kühn FE. Santos AM. Jogalekar AA. Pedro FM. Rigo P. Baratta W. J. Catal. 2004, 227: 253

4a Baratta W. Herrmann WA. Kratzer RM. Rigo P. Organometallics 2000, 19: 3664

4b Tutusaus O. Delfosse S. Demonceau A. Noels AF. Núñez R. Viñas C. Teixidor F. Tetrahedron Lett 2002, 43: 983

5 Kühn FE. Santos AM. Mini-Rev. Org. Chem. 2004, 1: 55

6a Treichel PM. Komar DA. Vincenti PJ. Synth. React. Inorg. Met.-Org. Chem. 1984, 14: 383

6b Lebel H. Marcoux J.-F. Molinaro C. Charette AB. Chem. Rev. 2003, 103: 977

7a Doyle MP. Forbes DC. Chem. Rev. 1998, 98: 911

7b Park SB. Nishiyama H. Itoh Y. Itoh K. J. Chem. Soc., Chem. Commun. 1994, 1315

7c Baratta W. del Zotto A. Rigo P. Chem. Commun. 1997, 2163

7d Maas G. Chem. Soc. Rev. 2004, 33: 183

8a Corma A. Garcia H. Chem. Rev. 2002, 102: 3837

8b de Vos DE. Dams M. Sels BF. Jacobs PA. Chem. Rev. 2002, 102: 3615

8c Leadbeater NE. Marco M. Chem. Rev. 2002, 102: 3217

9 Kresge CT. Leonowicz ME. Roth WJ. Vartuli JC. Beck JS. Nature 1992, 359: 710

10a Ryoo R. Joo SH. Kim JM. J. Phys. Chem. B 1999, 103: 7435

10b Sakthivel A. Selvam P. J. Catal. 2002, 211: 134

10c Sakthivel A. Selvam P. Catal. Lett. 2002, 84: 37

10d Sakthivel A. Zhao J. Hanzlik M. Kühn FE. Dalton Trans. 2004, 3338

10e Sakthivel A. Zhao J. Hanzlik M. Chiang AST. Herrmann WA. Kühn FE. Adv. Synth. Catal. 2005, 347: 473

10f Sakthivel A. Huang SJ. Chen WH. Huang LZ. Chen KH. Lin HP. Mou CY. Liu SB. Adv. Funct. Mater. 2005, 15: 253

11a Moller K. Bein T. Chem. Mater. 1998, 10: 2950

11b Bianchini C. Barbaro P. Top. Catal. 2002, 19: 17

11c Li C. Catal. Rev. - Sci. Eng. 2004, 46: 419

11d Kühn FE. Santos AM. Herrmann WA. Dalton Trans. 2005, 2483

12a Hansen CB. Hoogers GJ. Drenth W. J. Mol. Catal. 1993, 79: 153

12b Liu C.-J. Li S.-G. Pang W.-Q. Che C.-M. Chem. Commun. 1997, 65

12c Liu C.-J. Yu W.-Y. Li S.-G. Che C.-M. J. Org. Chem. 1998, 63: 7364

12d Yu X.-Q. Huang J.-S. Yu W.-Y. Che C.-M. J. Am. Chem. Soc. 2000, 122: 5337

12e Nestler O. Severin K. Org. Lett. 2001, 3: 3907

12f Zhang J.-L. Che C.-M. Org. Lett. 2002, 4: 1911

12g Zhang JL. Liu YL. Che CM. Chem. Commun. 2002, 2906

12h Fujishima K. Fukuoda A. Yamagishi A. Inagaki S. Fukushima Y. Ichikawa M. J. Mol. Catal. A: Chem. 2001, 166: 211

12i Brühwiler D. Frei H. J. Phys. Chem. B 2003, 107: 8547

13 Edwards HGM. Lewis IR. Turner PH. Inorg. Chim. Acta 1994, 216: 191

14 Sing KSW. Everett DH. Haul RAW. Moscow L. Pierotti RA. Rouquerol T. Siemienewska T. Pure Appl. Chem. 1985, 57: 603

Heterogenization of (η 5 -C 5 Me 5 )Ru(PPh 3 ) 2 Cl and Its Catalytic Application for Cyclopropanation of Styrene Using Ethyl Diazoacetate

Heterogenization of (η ⁵ -C ₅ Me ₅ )Ru(PPh ₃ ) ₂ Cl and Its Catalytic Application for Cyclopropanation of Styrene Using Ethyl Diazoacetate