A silica gel-supported ruthenium complex of 1,4,7-Trimethyl-1,4,7-triazacyclononane as recyclable catalyst for chemoselective oxidation of alcohols and alkenes by tert-butyl hydroperoxide

Journal of Organic Chemistry

Volumn 67, Issue 22, 2002, Pages 7716-7723

  Cheung, Wai Hung ^a   Yu, Wing Yiu ^a   Yip, Wing Ping ^a   Zhu, Nian Yong ^a   Che, Chi Ming ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDATION;

ADSORPTION; ALCOHOLS; ALDEHYDES; CATALYST SELECTIVITY; CATALYSTS; HYDROXYLATION; KETONES; MASS SPECTROMETRY; OLEFINS; OXIDATION; PEROXIDES; PHENOLS; RAMAN SPECTROSCOPY; RUTHENIUM; SILICA GEL; X RAY DIFFRACTION ANALYSIS;

ORGANOMETALLICS;

1,4,7 TRIMETHYL 1,4,7 TRIAZACYCLONONANE; ALCOHOL DERIVATIVE; ALKANE DERIVATIVE; ALKENE DERIVATIVE; RUTHENIUM COMPLEX; SILICA GEL; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL BINDING; COMPLEX FORMATION; DIFFUSE REFLECTANCE SPECTROSCOPY; HYDROXYLATION; OXIDATION; RAMAN SPECTROMETRY; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

EID: 0036827711     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0204404     Document Type: Article

References (112)

1. (a) Lee, T. V. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S. V., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 291.
2. (b) Ley, S. V.; Madin, A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Levy, S. V., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 251.
3. (c) Mijs, W. J.; DeJonge, C. R. H. I. Organic Synthesis with Metal Compounds; Plenum: New York, 1986.
4. (d) Sheldon, R. A.; Kochi, J. K. In Metal-Catalyzed Oxidation of Organic Compounds; Academic Press: New York, 1981.
5. (a) Rao, A. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S. V., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 357.
6. (b) Ullmann's Encyclopedia of Industrial Chemistry, 5th Ed.; Gerhartz, W., Yamamoto, Y. S., Kandy, L., Rounsaville, J. F., Schulz, G., Eds.; Verlag Chemie: Weinheim, 1987; Vol. A9, p 531.
7. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
8. (a) Applications of Hydrogen Peroxide and Derivatives; Jones, C. W.; The Royal Society of Chemistry: Cambridge, 1999.
9. (b) Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Strukul, G., Ed.; Kluwer: Dordrecht, The Netherland, 1992.
10. Selected examples for Mo(VI)/W(VI)-catalyzed organic oxidations, see: (a) Jost, C.; Wahl, G.; Kleinhenz, D.; Sundermeyer, J. In Peroxide Chemistry; Adam, W. Ed.; Wiley-VCH: Weinheim.; 2000, p 341. (b) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386 and references therein. (c) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (d) Bailey, A. J.; Griffith, W. P.; Parkin, B. C. J. Chem. Soc., Dalton Trans. 1995, 1833. (e) Venturello, C.; D'Aloisio, R. J. Org. Chem. 1988, 53, 1553. (f) Bortolini, O.; Conte, V.; Di Furia, F.; Modena, G. J. Org. Chem. 1986, 51, 2661. For alkene epoxidations, see: (g) Venturello, C.; Alneri, E.; Ricci, M. J. Org. Chem. 1983, 48, 3831.
11. Selected examples for Mo(VI)/W(VI)-catalyzed organic oxidations, see: (a) Jost, C.; Wahl, G.; Kleinhenz, D.; Sundermeyer, J. In Peroxide Chemistry; Adam, W. Ed.; Wiley-VCH: Weinheim.; 2000, p 341. (b) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386 and references therein. (c) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (d) Bailey, A. J.; Griffith, W. P.; Parkin, B. C. J. Chem. Soc., Dalton Trans. 1995, 1833. (e) Venturello, C.; D'Aloisio, R. J. Org. Chem. 1988, 53, 1553. (f) Bortolini, O.; Conte, V.; Di Furia, F.; Modena, G. J. Org. Chem. 1986, 51, 2661. For alkene epoxidations, see: (g) Venturello, C.; Alneri, E.; Ricci, M. J. Org. Chem. 1983, 48, 3831.
12. Selected examples for Mo(VI)/W(VI)-catalyzed organic oxidations, see: (a) Jost, C.; Wahl, G.; Kleinhenz, D.; Sundermeyer, J. In Peroxide Chemistry; Adam, W. Ed.; Wiley-VCH: Weinheim.; 2000, p 341. (b) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386 and references therein. (c) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (d) Bailey, A. J.; Griffith, W. P.; Parkin, B. C. J. Chem. Soc., Dalton Trans. 1995, 1833. (e) Venturello, C.; D'Aloisio, R. J. Org. Chem. 1988, 53, 1553. (f) Bortolini, O.; Conte, V.; Di Furia, F.; Modena, G. J. Org. Chem. 1986, 51, 2661. For alkene epoxidations, see: (g) Venturello, C.; Alneri, E.; Ricci, M. J. Org. Chem. 1983, 48, 3831.
13. Selected examples for Mo(VI)/W(VI)-catalyzed organic oxidations, see: (a) Jost, C.; Wahl, G.; Kleinhenz, D.; Sundermeyer, J. In Peroxide Chemistry; Adam, W. Ed.; Wiley-VCH: Weinheim.; 2000, p 341. (b) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386 and references therein. (c) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (d) Bailey, A. J.; Griffith, W. P.; Parkin, B. C. J. Chem. Soc., Dalton Trans. 1995, 1833. (e) Venturello, C.; D'Aloisio, R. J. Org. Chem. 1988, 53, 1553. (f) Bortolini, O.; Conte, V.; Di Furia, F.; Modena, G. J. Org. Chem. 1986, 51, 2661. For alkene epoxidations, see: (g) Venturello, C.; Alneri, E.; Ricci, M. J. Org. Chem. 1983, 48, 3831.
14. Selected examples for Mo(VI)/W(VI)-catalyzed organic oxidations, see: (a) Jost, C.; Wahl, G.; Kleinhenz, D.; Sundermeyer, J. In Peroxide Chemistry; Adam, W. Ed.; Wiley-VCH: Weinheim.; 2000, p 341. (b) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386 and references therein. (c) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (d) Bailey, A. J.; Griffith, W. P.; Parkin, B. C. J. Chem. Soc., Dalton Trans. 1995, 1833. (e) Venturello, C.; D'Aloisio, R. J. Org. Chem. 1988, 53, 1553. (f) Bortolini, O.; Conte, V.; Di Furia, F.; Modena, G. J. Org. Chem. 1986, 51, 2661. For alkene epoxidations, see: (g) Venturello, C.; Alneri, E.; Ricci, M. J. Org. Chem. 1983, 48, 3831.
15. Selected examples for Mo(VI)/W(VI)-catalyzed organic oxidations, see: (a) Jost, C.; Wahl, G.; Kleinhenz, D.; Sundermeyer, J. In Peroxide Chemistry; Adam, W. Ed.; Wiley-VCH: Weinheim.; 2000, p 341. (b) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386 and references therein. (c) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (d) Bailey, A. J.; Griffith, W. P.; Parkin, B. C. J. Chem. Soc., Dalton Trans. 1995, 1833. (e) Venturello, C.; D'Aloisio, R. J. Org. Chem. 1988, 53, 1553. (f) Bortolini, O.; Conte, V.; Di Furia, F.; Modena, G. J. Org. Chem. 1986, 51, 2661. For alkene epoxidations, see: (g) Venturello, C.; Alneri, E.; Ricci, M. J. Org. Chem. 1983, 48, 3831.
16. Selected examples for Mo(VI)/W(VI)-catalyzed organic oxidations, see: (a) Jost, C.; Wahl, G.; Kleinhenz, D.; Sundermeyer, J. In Peroxide Chemistry; Adam, W. Ed.; Wiley-VCH: Weinheim.; 2000, p 341. (b) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386 and references therein. (c) Sato, K.; Aoki, M.; Ogawa, M.; Hashimoto, T.; Noyori, R. J. Org. Chem. 1996, 61, 8310. (d) Bailey, A. J.; Griffith, W. P.; Parkin, B. C. J. Chem. Soc., Dalton Trans. 1995, 1833. (e) Venturello, C.; D'Aloisio, R. J. Org. Chem. 1988, 53, 1553. (f) Bortolini, O.; Conte, V.; Di Furia, F.; Modena, G. J. Org. Chem. 1986, 51, 2661. For alkene epoxidations, see: (g) Venturello, C.; Alneri, E.; Ricci, M. J. Org. Chem. 1983, 48, 3831.
17. 3-catalyzed organic oxidations, see: (a) Kuhn, F. E.; Herrmann, W. A. In Metal-Oxo and Metal-Peroxo Species in Catalytic Oxidations; Meunier, B. Ed.; Springer-Verlag: Berlin, 2000; p 213. (b) Saladino, R.; Neri, V.; Pelliccia, A. R.; Caminiti, R.; Sadun, C. J. Org. Chem. 2002, 67, 1323. (c) Zauche, T. H.; Espenson, J. H. Inorg. Chem. 1998, 37, 6827. (d) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189. (e) Murray, R. W.; Iyanar, K.; Chen, J.-X.; Wearing, J. T. Tetrahedron Lett. 1995, 36(36), 6415. (f) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
18. 3-catalyzed organic oxidations, see: (a) Kuhn, F. E.; Herrmann, W. A. In Metal-Oxo and Metal-Peroxo Species in Catalytic Oxidations; Meunier, B. Ed.; Springer-Verlag: Berlin, 2000; p 213. (b) Saladino, R.; Neri, V.; Pelliccia, A. R.; Caminiti, R.; Sadun, C. J. Org. Chem. 2002, 67, 1323. (c) Zauche, T. H.; Espenson, J. H. Inorg. Chem. 1998, 37, 6827. (d) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189. (e) Murray, R. W.; Iyanar, K.; Chen, J.-X.; Wearing, J. T. Tetrahedron Lett. 1995, 36(36), 6415. (f) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
19. 3-catalyzed organic oxidations, see: (a) Kuhn, F. E.; Herrmann, W. A. In Metal-Oxo and Metal-Peroxo Species in Catalytic Oxidations; Meunier, B. Ed.; Springer-Verlag: Berlin, 2000; p 213. (b) Saladino, R.; Neri, V.; Pelliccia, A. R.; Caminiti, R.; Sadun, C. J. Org. Chem. 2002, 67, 1323. (c) Zauche, T. H.; Espenson, J. H. Inorg. Chem. 1998, 37, 6827. (d) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189. (e) Murray, R. W.; Iyanar, K.; Chen, J.-X.; Wearing, J. T. Tetrahedron Lett. 1995, 36(36), 6415. (f) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
20. 3-catalyzed organic oxidations, see: (a) Kuhn, F. E.; Herrmann, W. A. In Metal-Oxo and Metal-Peroxo Species in Catalytic Oxidations; Meunier, B. Ed.; Springer-Verlag: Berlin, 2000; p 213. (b) Saladino, R.; Neri, V.; Pelliccia, A. R.; Caminiti, R.; Sadun, C. J. Org. Chem. 2002, 67, 1323. (c) Zauche, T. H.; Espenson, J. H. Inorg. Chem. 1998, 37, 6827. (d) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189. (e) Murray, R. W.; Iyanar, K.; Chen, J.-X.; Wearing, J. T. Tetrahedron Lett. 1995, 36(36), 6415. (f) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
21. 3-catalyzed organic oxidations, see: (a) Kuhn, F. E.; Herrmann, W. A. In Metal-Oxo and Metal-Peroxo Species in Catalytic Oxidations; Meunier, B. Ed.; Springer-Verlag: Berlin, 2000; p 213. (b) Saladino, R.; Neri, V.; Pelliccia, A. R.; Caminiti, R.; Sadun, C. J. Org. Chem. 2002, 67, 1323. (c) Zauche, T. H.; Espenson, J. H. Inorg. Chem. 1998, 37, 6827. (d) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189. (e) Murray, R. W.; Iyanar, K.; Chen, J.-X.; Wearing, J. T. Tetrahedron Lett. 1995, 36(36), 6415. (f) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
22. 3-catalyzed organic oxidations, see: (a) Kuhn, F. E.; Herrmann, W. A. In Metal-Oxo and Metal-Peroxo Species in Catalytic Oxidations; Meunier, B. Ed.; Springer-Verlag: Berlin, 2000; p 213. (b) Saladino, R.; Neri, V.; Pelliccia, A. R.; Caminiti, R.; Sadun, C. J. Org. Chem. 2002, 67, 1323. (c) Zauche, T. H.; Espenson, J. H. Inorg. Chem. 1998, 37, 6827. (d) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189. (e) Murray, R. W.; Iyanar, K.; Chen, J.-X.; Wearing, J. T. Tetrahedron Lett. 1995, 36(36), 6415. (f) Herrmann, W. A.; Fischer, R. W.; Marz, D. W. Angew. Chem., Int. Ed. Engl. 1991, 30, 1638.
23. 2, see for example: (a) Brinksma, J.; Hage, R.; Kerschner, J.; Feringa, B. L. Chem. Commun. 2000, 537. (b) Lane, B. S.; Burgess, K. J. Am. Chem. Soc. 2001, 123, 2933. (c) Berkessel, A.; Sklorz, C. A. Tetrahedron Lett. 1999, 40, 7965. (d) Zondervan, C.; Hage, R.; Feringa, B. L. Chem. Commun. 1997, 419. Selected examples for Mn-catalyzed alkene epoxidations, see: (e) De Vos, D.; Bein, T. Chem. Commun. 1996, 917.
24. 2, see for example: (a) Brinksma, J.; Hage, R.; Kerschner, J.; Feringa, B. L. Chem. Commun. 2000, 537. (b) Lane, B. S.; Burgess, K. J. Am. Chem. Soc. 2001, 123, 2933. (c) Berkessel, A.; Sklorz, C. A. Tetrahedron Lett. 1999, 40, 7965. (d) Zondervan, C.; Hage, R.; Feringa, B. L. Chem. Commun. 1997, 419. Selected examples for Mn-catalyzed alkene epoxidations, see: (e) De Vos, D.; Bein, T. Chem. Commun. 1996, 917.
25. 2, see for example: (a) Brinksma, J.; Hage, R.; Kerschner, J.; Feringa, B. L. Chem. Commun. 2000, 537. (b) Lane, B. S.; Burgess, K. J. Am. Chem. Soc. 2001, 123, 2933. (c) Berkessel, A.; Sklorz, C. A. Tetrahedron Lett. 1999, 40, 7965. (d) Zondervan, C.; Hage, R.; Feringa, B. L. Chem. Commun. 1997, 419. Selected examples for Mn-catalyzed alkene epoxidations, see: (e) De Vos, D.; Bein, T. Chem. Commun. 1996, 917.
26. 2, see for example: (a) Brinksma, J.; Hage, R.; Kerschner, J.; Feringa, B. L. Chem. Commun. 2000, 537. (b) Lane, B. S.; Burgess, K. J. Am. Chem. Soc. 2001, 123, 2933. (c) Berkessel, A.; Sklorz, C. A. Tetrahedron Lett. 1999, 40, 7965. (d) Zondervan, C.; Hage, R.; Feringa, B. L. Chem. Commun. 1997, 419. Selected examples for Mn-catalyzed alkene epoxidations, see: (e) De Vos, D.; Bein, T. Chem. Commun. 1996, 917.
27. 2, see for example: (a) Brinksma, J.; Hage, R.; Kerschner, J.; Feringa, B. L. Chem. Commun. 2000, 537. (b) Lane, B. S.; Burgess, K. J. Am. Chem. Soc. 2001, 123, 2933. (c) Berkessel, A.; Sklorz, C. A. Tetrahedron Lett. 1999, 40, 7965. (d) Zondervan, C.; Hage, R.; Feringa, B. L. Chem. Commun. 1997, 419. Selected examples for Mn-catalyzed alkene epoxidations, see: (e) De Vos, D.; Bein, T. Chem. Commun. 1996, 917.
28. 2: (a) Gupta, S. S.; Stadler, M.; Noser, C. A.; Ghosh, A.; Steinhoff, B.; Lenoir, D.; Horwitz, C. P.; Schramm, K.-W.; Collins, T. J. Science 2002, 296, 326. (b) White, M. C.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 7194.
29. 2: (a) Gupta, S. S.; Stadler, M.; Noser, C. A.; Ghosh, A.; Steinhoff, B.; Lenoir, D.; Horwitz, C. P.; Schramm, K.-W.; Collins, T. J. Science 2002, 296, 326. (b) White, M. C.; Doyle, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2001, 123, 7194.
30. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
31. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
32. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
33. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
34. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
35. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
36. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
37. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
38. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
39. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
40. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
41. 2 as oxidant, see for examples: (g) Dijksman, A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 1591. (h) Lai, T.-S.; Zhang, R.; Cheung, K.-K.; Kwong, H.-L.; Che, C.-M. Chem. Commun. 1998, 1583. (i) Hanyu, A.; Takezawa, E.; Sakaguchi, S.; Ishii, Y. Tetrahedron Lett. 1998, 39, 5557. (j) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chellé-Regnaut, I.; Urch, C. J.; Brown, S. M. J. Am. Chem. Soc. 1997, 119, 12661. (k) Bilgrien, C.; Davis, S.; Drago, R. S. J. Am. Chem. Soc. 1987, 109, 3786. (l) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
42. For Pd-catalyzed aerobic alcohol oxidations: (a) Brink, G.-J. t.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (b) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011.
43. For Pd-catalyzed aerobic alcohol oxidations: (a) Brink, G.-J. t.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (b) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011.
44. For Pd-catalyzed aerobic alcohol oxidations: (a) Brink, G.-J. t.; Arends, I. W. C. E.; Sheldon, R. A. Science 2000, 287, 1636. (b) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. J. Org. Chem. 1999, 64, 6750. (c) Nishimura, T.; Onoue, T.; Ohe, K.; Uemura, S. Tetrahedron Lett. 1998, 39, 6011.
45. For Cu-catalyzed aerobic alcohol oxidations: (a) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, I.; Gautier, A.; Brown, S. M.; Urch, C. J. J. Org. Chem. 1999, 64, 2433. (b) Markô, I. E.; Gautier, A.; Chelle-Regnaut, I.; Giles, P. R.; Tsukazaki, M.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1998, 63, 7576. (c) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M,; Urch, C. J. Science 1996, 274, 2044.
46. For Cu-catalyzed aerobic alcohol oxidations: (a) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, I.; Gautier, A.; Brown, S. M.; Urch, C. J. J. Org. Chem. 1999, 64, 2433. (b) Markô, I. E.; Gautier, A.; Chelle-Regnaut, I.; Giles, P. R.; Tsukazaki, M.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1998, 63, 7576. (c) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M,; Urch, C. J. Science 1996, 274, 2044.
47. For Cu-catalyzed aerobic alcohol oxidations: (a) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Chelle-Regnaut, I.; Gautier, A.; Brown, S. M.; Urch, C. J. J. Org. Chem. 1999, 64, 2433. (b) Markô, I. E.; Gautier, A.; Chelle-Regnaut, I.; Giles, P. R.; Tsukazaki, M.; Urch, C. J.; Brown, S. M. J. Org. Chem. 1998, 63, 7576. (c) Markô, I. E.; Giles, P. R.; Tsukazaki, M.; Brown, S. M,; Urch, C. J. Science 1996, 274, 2044.
48. (a) Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.
49. (b) Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
50. (c) Griffith, W. P. Chem. Soc. Rev. 1992, 21, 179.
51. Groves, J. T.; Roman, J. S. J. Am. Chem. Soc. 1995, 117, 5594.
52. For alkene epoxidations, see: (a) Ohtake, H.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 2521. (b) Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1991, 32, 7435. (c) Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1989, 30, 6545. For alkane hydroxylations see: (d) Higuchi, T.; Hirobe, M. J. Mol. Catal. (A) 1996, 113, 403. (e) Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc. 1992, 114, 10660.
53. For alkene epoxidations, see: (a) Ohtake, H.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 2521. (b) Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1991, 32, 7435. (c) Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1989, 30, 6545. For alkane hydroxylations see: (d) Higuchi, T.; Hirobe, M. J. Mol. Catal. (A) 1996, 113, 403. (e) Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc. 1992, 114, 10660.
54. For alkene epoxidations, see: (a) Ohtake, H.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 2521. (b) Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1991, 32, 7435. (c) Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1989, 30, 6545. For alkane hydroxylations see: (d) Higuchi, T.; Hirobe, M. J. Mol. Catal. (A) 1996, 113, 403. (e) Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc. 1992, 114, 10660.
55. For alkene epoxidations, see: (a) Ohtake, H.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 2521. (b) Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1991, 32, 7435. (c) Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1989, 30, 6545. For alkane hydroxylations see: (d) Higuchi, T.; Hirobe, M. J. Mol. Catal. (A) 1996, 113, 403. (e) Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc. 1992, 114, 10660.
56. For alkene epoxidations, see: (a) Ohtake, H.; Higuchi, T.; Hirobe, M. Tetrahedron Lett. 1992, 33, 2521. (b) Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1991, 32, 7435. (c) Higuchi, T.; Ohtake, H.; Hirobe, M. Tetrahedron Lett. 1989, 30, 6545. For alkane hydroxylations see: (d) Higuchi, T.; Hirobe, M. J. Mol. Catal. (A) 1996, 113, 403. (e) Ohtake, H.; Higuchi, T.; Hirobe, M. J. Am. Chem. Soc. 1992, 114, 10660.
57. Recent examples on chiral ruthenium porphyrin-mediated asymmetric oxidations using aromatic N-oxides as oxidant: (a) Zhang, R.; Yu, W.-Y.; Wong, K.-Y.; Che, C.-M. J. Org. Chem. 2001, 66, 8145. (b) Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. Chem. Commun. 1999, 1791. (c) Zhang, R. Yu, W.-Y. Lai, T.-S. C.-M. Che, Chem. Commun. 1999, 409. (d) Gross, Z. Ini, S. Org. Lett. 1999, 1, 2077. (e) Gross, Z. Ini, S. J. Org. Chem. 1997, 62, 5514. (f) Berkessel, A. Frauenkron, M. J. Chem. Soc., Perkin Trans. 1 1997, 2265. (g) Gross, Z. Ini, S. Kapon, M. Cohen, S. Tetrahedron Lett. 1996, 37, 7325.
58. Recent examples on chiral ruthenium porphyrin-mediated asymmetric oxidations using aromatic N-oxides as oxidant: (a) Zhang, R.; Yu, W.-Y.; Wong, K.-Y.; Che, C.-M. J. Org. Chem. 2001, 66, 8145. (b) Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. Chem. Commun. 1999, 1791. (c) Zhang, R. Yu, W.-Y. Lai, T.-S. C.-M. Che, Chem. Commun. 1999, 409. (d) Gross, Z. Ini, S. Org. Lett. 1999, 1, 2077. (e) Gross, Z. Ini, S. J. Org. Chem. 1997, 62, 5514. (f) Berkessel, A. Frauenkron, M. J. Chem. Soc., Perkin Trans. 1 1997, 2265. (g) Gross, Z. Ini, S. Kapon, M. Cohen, S. Tetrahedron Lett. 1996, 37, 7325.
59. Recent examples on chiral ruthenium porphyrin-mediated asymmetric oxidations using aromatic N-oxides as oxidant: (a) Zhang, R.; Yu, W.-Y.; Wong, K.-Y.; Che, C.-M. J. Org. Chem. 2001, 66, 8145. (b) Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. Chem. Commun. 1999, 1791. (c) Zhang, R. Yu, W.-Y. Lai, T.-S. C.-M. Che, Chem. Commun. 1999, 409. (d) Gross, Z. Ini, S. Org. Lett. 1999, 1, 2077. (e) Gross, Z. Ini, S. J. Org. Chem. 1997, 62, 5514. (f) Berkessel, A. Frauenkron, M. J. Chem. Soc., Perkin Trans. 1 1997, 2265. (g) Gross, Z. Ini, S. Kapon, M. Cohen, S. Tetrahedron Lett. 1996, 37, 7325.
60. Recent examples on chiral ruthenium porphyrin-mediated asymmetric oxidations using aromatic N-oxides as oxidant: (a) Zhang, R.; Yu, W.-Y.; Wong, K.-Y.; Che, C.-M. J. Org. Chem. 2001, 66, 8145. (b) Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. Chem. Commun. 1999, 1791. (c) Zhang, R. Yu, W.-Y. Lai, T.-S. C.-M. Che, Chem. Commun. 1999, 409. (d) Gross, Z. Ini, S. Org. Lett. 1999, 1, 2077. (e) Gross, Z. Ini, S. J. Org. Chem. 1997, 62, 5514. (f) Berkessel, A. Frauenkron, M. J. Chem. Soc., Perkin Trans. 1 1997, 2265. (g) Gross, Z. Ini, S. Kapon, M. Cohen, S. Tetrahedron Lett. 1996, 37, 7325.
61. Recent examples on chiral ruthenium porphyrin-mediated asymmetric oxidations using aromatic N-oxides as oxidant: (a) Zhang, R.; Yu, W.-Y.; Wong, K.-Y.; Che, C.-M. J. Org. Chem. 2001, 66, 8145. (b) Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. Chem. Commun. 1999, 1791. (c) Zhang, R. Yu, W.-Y. Lai, T.-S. C.-M. Che, Chem. Commun. 1999, 409. (d) Gross, Z. Ini, S. Org. Lett. 1999, 1, 2077. (e) Gross, Z. Ini, S. J. Org. Chem. 1997, 62, 5514. (f) Berkessel, A. Frauenkron, M. J. Chem. Soc., Perkin Trans. 1 1997, 2265. (g) Gross, Z. Ini, S. Kapon, M. Cohen, S. Tetrahedron Lett. 1996, 37, 7325.
62. Recent examples on chiral ruthenium porphyrin-mediated asymmetric oxidations using aromatic N-oxides as oxidant: (a) Zhang, R.; Yu, W.-Y.; Wong, K.-Y.; Che, C.-M. J. Org. Chem. 2001, 66, 8145. (b) Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. Chem. Commun. 1999, 1791. (c) Zhang, R. Yu, W.-Y. Lai, T.-S. C.-M. Che, Chem. Commun. 1999, 409. (d) Gross, Z. Ini, S. Org. Lett. 1999, 1, 2077. (e) Gross, Z. Ini, S. J. Org. Chem. 1997, 62, 5514. (f) Berkessel, A. Frauenkron, M. J. Chem. Soc., Perkin Trans. 1 1997, 2265. (g) Gross, Z. Ini, S. Kapon, M. Cohen, S. Tetrahedron Lett. 1996, 37, 7325.
63. Recent examples on chiral ruthenium porphyrin-mediated asymmetric oxidations using aromatic N-oxides as oxidant: (a) Zhang, R.; Yu, W.-Y.; Wong, K.-Y.; Che, C.-M. J. Org. Chem. 2001, 66, 8145. (b) Zhang, R.; Yu, W.-Y.; Lai, T.-S.; Che, C.-M. Chem. Commun. 1999, 1791. (c) Zhang, R. Yu, W.-Y. Lai, T.-S. C.-M. Che, Chem. Commun. 1999, 409. (d) Gross, Z. Ini, S. Org. Lett. 1999, 1, 2077. (e) Gross, Z. Ini, S. J. Org. Chem. 1997, 62, 5514. (f) Berkessel, A. Frauenkron, M. J. Chem. Soc., Perkin Trans. 1 1997, 2265. (g) Gross, Z. Ini, S. Kapon, M. Cohen, S. Tetrahedron Lett. 1996, 37, 7325.
64. For other heterogeneous Ru catalysts for organic oxidations, see: (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J, Am. Chem. Soc. 2000, 122, 7144. (b) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750. (d) Dalal. M. K.; Upadhyay, M. J.; Ram, R. N. J. Mol. Catal. (A) 1999, 142, 325. (e) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907. (f) Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977. (g) Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364. (h) Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. J. Chem. Soc., Chem. Commun. 1997, 65. (i) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 1907.
65. For other heterogeneous Ru catalysts for organic oxidations, see: (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J, Am. Chem. Soc. 2000, 122, 7144. (b) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750. (d) Dalal. M. K.; Upadhyay, M. J.; Ram, R. N. J. Mol. Catal. (A) 1999, 142, 325. (e) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907. (f) Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977. (g) Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364. (h) Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. J. Chem. Soc., Chem. Commun. 1997, 65. (i) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 1907.
66. For other heterogeneous Ru catalysts for organic oxidations, see: (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J, Am. Chem. Soc. 2000, 122, 7144. (b) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750. (d) Dalal. M. K.; Upadhyay, M. J.; Ram, R. N. J. Mol. Catal. (A) 1999, 142, 325. (e) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907. (f) Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977. (g) Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364. (h) Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. J. Chem. Soc., Chem. Commun. 1997, 65. (i) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 1907.
67. For other heterogeneous Ru catalysts for organic oxidations, see: (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J, Am. Chem. Soc. 2000, 122, 7144. (b) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750. (d) Dalal. M. K.; Upadhyay, M. J.; Ram, R. N. J. Mol. Catal. (A) 1999, 142, 325. (e) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907. (f) Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977. (g) Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364. (h) Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. J. Chem. Soc., Chem. Commun. 1997, 65. (i) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 1907.
68. For other heterogeneous Ru catalysts for organic oxidations, see: (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J, Am. Chem. Soc. 2000, 122, 7144. (b) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750. (d) Dalal. M. K.; Upadhyay, M. J.; Ram, R. N. J. Mol. Catal. (A) 1999, 142, 325. (e) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907. (f) Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977. (g) Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364. (h) Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. J. Chem. Soc., Chem. Commun. 1997, 65. (i) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 1907.
69. For other heterogeneous Ru catalysts for organic oxidations, see: (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J, Am. Chem. Soc. 2000, 122, 7144. (b) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750. (d) Dalal. M. K.; Upadhyay, M. J.; Ram, R. N. J. Mol. Catal. (A) 1999, 142, 325. (e) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907. (f) Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977. (g) Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364. (h) Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. J. Chem. Soc., Chem. Commun. 1997, 65. (i) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 1907.
70. For other heterogeneous Ru catalysts for organic oxidations, see: (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J, Am. Chem. Soc. 2000, 122, 7144. (b) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750. (d) Dalal. M. K.; Upadhyay, M. J.; Ram, R. N. J. Mol. Catal. (A) 1999, 142, 325. (e) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907. (f) Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977. (g) Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364. (h) Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. J. Chem. Soc., Chem. Commun. 1997, 65. (i) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 1907.
71. For other heterogeneous Ru catalysts for organic oxidations, see: (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J, Am. Chem. Soc. 2000, 122, 7144. (b) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750. (d) Dalal. M. K.; Upadhyay, M. J.; Ram, R. N. J. Mol. Catal. (A) 1999, 142, 325. (e) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907. (f) Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977. (g) Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364. (h) Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. J. Chem. Soc., Chem. Commun. 1997, 65. (i) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 1907.
72. For other heterogeneous Ru catalysts for organic oxidations, see: (a) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J, Am. Chem. Soc. 2000, 122, 7144. (b) Matsushita, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 1999, 265. (c) Kaneda, K.; Yamashita, T.; Matsushita, T.; Ebitani, K. J. Org. Chem. 1998, 63, 1750. (d) Dalal. M. K.; Upadhyay, M. J.; Ram, R. N. J. Mol. Catal. (A) 1999, 142, 325. (e) Bleloch, A.; Johnson, B. F. G.; Ley, S. V.; Price, A. J.; Shephard, D. S.; Thomas, A. W. Chem. Commun. 1999, 1907. (f) Hinzen, B.; Lenz, R.; Ley, S. V. Synthesis 1998, 977. (g) Liu, C.-J.; Yu, W.-Y.; Li, S.-G.; Che, C.-M. J. Org. Chem. 1998, 63, 7364. (h) Liu, C.-J.; Li, S.-G.; Pang, W.-Q.; Che, C.-M. J. Chem. Soc., Chem. Commun. 1997, 65. (i) Hinzen, B.; Ley, S. V. J. Chem. Soc., Perkin Trans. 1 1997, 1907.
73. (a) Che, C.-M.; Yu, W.-Y. Pure Appl. Chem. 1999, 71, 281.
74. (b) Che, C.-M.; Yam, V. W.-W. Adv. Transition Metal Coord. Chem. 1996, 1, 209.
75. (c) Che, C.-M.; Yam, V. W.-W. Adv. Inorg. Chem. 1992, 39, 233.
76. (a) Che, C.-M.; Yu, W.-Y.; Chan, P.-M.; Cheng, W.-C.; Peng, S.-M.; Lau, K.-C.; Li, W.-K. J. Am. Chem. Soc. 2000, 122, 11380.
77. (b) Fung, W.-H.; Yu, W.-Y.; Che, C.-M. J. Org. Chem. 1998, 63, 7715.
78. (c) Cheng, W.-C.; Yu, W.-Y.; Li, C.-K.; Che, C.-M. J. Org. Chem. 1995, 60, 6840.
79. (d) Cheng, W.-C.; Yu, W.-Y.; Cheung, K.-K.; Che, C.-M. J. Chem. Soc., Chem. Commun. 1994, 1063.
80. (e) Che, C.-M.; Tang, W.-T.; Lee, W.-O, Wong, K.-Y.; Lau, T.-C. J. Chem. Soc., Dalton Trans. 1992, 1551.
81. (f) Che, C.-M.; Li, C.-K.; Tang, W.-T.; Yu, W.-Y. J. Chem. Soc., Dalton Trans. 1992, 3153.
82. (g) Che, C.-M.; Lau, T.-C.; Ho, C. J. Chem. Soc., Dalton Trans. 1991, 1901.
83. (h) Che, C.-M.; Yam, V. W.-W.; Mak, T. C.-W. J. Am. Chem. Soc. 1990, 112, 2284.
84. (i) Che, C.-M.; Ho, C.; Lau, T.-C. J. Chem. Soc., Dalton Trans. 1991, 1259.
85. (a) Lebeau, E. L.; Meyer, T. J. Inorg. Chem. 1999, 38, 2174.
86. (b) Stultz, L. K.; Binstead, R. A.; Reynolds, M. S.; Meyer, T. J. J. Am. Chem. Soc. 1995, 117, 2520.
87. (c) Roecker, L.; Meyer, T. J. J. Am. Chem. Soc. 1987, 109, 746.
88. (d) Dobson, J. C.; Seok, W. K.; Meyer, T. J. Inorg. Chem. 1986, 25, 1513.
89. Sharpless, K. B.; Verhoeven, T. R. Aldrichimica Acta 1979, 12-(4), 201.
90. Banerjee, A. K.; Laya Mimó, M. S.; Vera Vegas, W. J. Russ. Chem. Rev. 2001, 70, 971.
91. Schinzer, D.; Kalesse, M.; Kabbara, J. Tetrahedron Lett. 1988, 29, 5241.
92. Brillon, D.; Sauve, G. J. Org. Chem. 1992, 57, 1838.
93. Cheng, W.-C.; Yu, W.-Y.; Cheung, K.-K.; Che, C.-M. J. Chem. Soc., Dalton Trans. 1994, 57.
94. Bernhard, P.; Bürgi, H.-B.; Hauser, J.; Lehmann, H.; Ludi, A. Inorg. Chem. 1982, 21, 3936.
95. Grover, N.; Gupta, N.; Singh, P.; Thorp, H. H. Inorg. Chem. 1992, 31, 2014.
96. Chiu, W.-H.; Che, C.-M.; Mak, T. C.-W. Polyhedron 1996, 15, 1129.
97. Krohn, K.; Vinke, I.; Adam, H. J. Org. Chem. 1996, 61, 1467.
98. Tidwell, T. T. Synthesis 1990, 10, 857.
99. Neubold, P.; Wieghardt, K. Nuber, B.; Weiss, J. Angew. Chem., Int. Ed. Engl. 1988, 27, 933.
100. Murugavel, R.; Roesky, H. W. Angew. Chem., Int. Ed. Engl. 1997, 36, 477 and references therein.
101. For reviews of dioxirane chemistry, see: (a) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, 1990; Vol. 2, p 1. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (c) Murray, R. W. Chem. Rev. 1989, 89, 1187.
102. For reviews of dioxirane chemistry, see: (a) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, 1990; Vol. 2, p 1. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (c) Murray, R. W. Chem. Rev. 1989, 89, 1187.
103. For reviews of dioxirane chemistry, see: (a) Curci, R. In Advances in Oxygenated Processes; Baumstark, A. L., Ed.; JAI Press: Greenwich, 1990; Vol. 2, p 1. (b) Adam, W.; Curci, R.; Edwards, J. O. Acc. Chem. Res. 1989, 22, 205. (c) Murray, R. W. Chem. Rev. 1989, 89, 1187.
104. (a) Hudlicky, M. Oxidations in Organic Chemistry; American Chemical Society: Washington, D. C. 1990; p 163.
105. (b) Whiting D. A. In Comprehensive Organic Chemistry; Stoddart, F., Ed.; Pergamon: Oxford, 1979; Vol. 1, p 707.
106. (c) Harborne, J. B. Biochemistry of Phenolic Compounds; Academic Press: London, 1964.
107. (d) Pridham, J. B. Enzyme Chemistry of Phenolic Compounds; Pergamon: New York, 1963.
108. (a) Ingold, K. U. In Free Radicals; Kochi, J. K., Ed.; John Wiley & Sons: New York, 1973; Vol. 1, p 37.
109. (b) Taylor, W. I.; Battersby, A. R. Oxidative Coupling of Phenols; Marcel Dekker: New York, 1967.
110. Murahashi, S.-I.; Naota, T.; Miyaguchi, N.; Noda, S. J. Am. Chem. Soc. 1996, 118, 2509.
111. Examples for phenol oxidation by peroxo-copper complexes to form discrete catechol intermediates, see: (a) Mandal, S.; Macikenas, D.; Protasiewicz, J. D.; Sayre, L. M. J. Org. Chem. 2000, 65, 4804. (b) Berreau, L. M.; Mahapatra, S.; Halfen, J. A.; Houser, R. P.; Young, V. G., Jr.; Tolman, W. B. Angew. Chem., Int. Ed. 1999, 38, 207.
112. Examples for phenol oxidation by peroxo-copper complexes to form discrete catechol intermediates, see: (a) Mandal, S.; Macikenas, D.; Protasiewicz, J. D.; Sayre, L. M. J. Org. Chem. 2000, 65, 4804. (b) Berreau, L. M.; Mahapatra, S.; Halfen, J. A.; Houser, R. P.; Young, V. G., Jr.; Tolman, W. B. Angew. Chem., Int. Ed. 1999, 38, 207.