A catalytic system for reductive transformations via one-electron transfer

Synlett

Volumn , Issue 2, 1999, Pages 175-181

  Hirao, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Catalyst; One electron reduction; Pinacol coupling; Radical; Redox

Indexed keywords

CHROMIUM; RADICAL; TITANIUM; VANADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL BOND; CYCLIZATION; DEHALOGENATION; DIMERIZATION; ELECTRON TRANSPORT; HYDROGENATION; RECYCLING; REDUCTION; STEREOCHEMISTRY;

EID: 0032955135     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2567     Document Type: Article

References (53)

1. Ho, T.-L. Synthesis 1979, 1; Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; Freeman, F. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; Chapter 1; Pons, J.-M; Santelli, M. Tetrahedron 1988, 44, 4295; Rehder, D.; Gailus, H. Trends in Organometallic Chemistry 1994, 1, 397; Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519; Dalko, P. I. Tetrahedron 1995, 51, 7579.
2. Ho, T.-L. Synthesis 1979, 1; Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; Freeman, F. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; Chapter 1; Pons, J.-M; Santelli, M. Tetrahedron 1988, 44, 4295; Rehder, D.; Gailus, H. Trends in Organometallic Chemistry 1994, 1, 397; Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519; Dalko, P. I. Tetrahedron 1995, 51, 7579.
3. Ho, T.-L. Synthesis 1979, 1; Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; Freeman, F. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; Chapter 1; Pons, J.-M; Santelli, M. Tetrahedron 1988, 44, 4295; Rehder, D.; Gailus, H. Trends in Organometallic Chemistry 1994, 1, 397; Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519; Dalko, P. I. Tetrahedron 1995, 51, 7579.
4. Ho, T.-L. Synthesis 1979, 1; Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; Freeman, F. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; Chapter 1; Pons, J.-M; Santelli, M. Tetrahedron 1988, 44, 4295; Rehder, D.; Gailus, H. Trends in Organometallic Chemistry 1994, 1, 397; Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519; Dalko, P. I. Tetrahedron 1995, 51, 7579.
5. Ho, T.-L. Synthesis 1979, 1; Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; Freeman, F. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; Chapter 1; Pons, J.-M; Santelli, M. Tetrahedron 1988, 44, 4295; Rehder, D.; Gailus, H. Trends in Organometallic Chemistry 1994, 1, 397; Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519; Dalko, P. I. Tetrahedron 1995, 51, 7579.
6. Ho, T.-L. Synthesis 1979, 1; Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; Freeman, F. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; Chapter 1; Pons, J.-M; Santelli, M. Tetrahedron 1988, 44, 4295; Rehder, D.; Gailus, H. Trends in Organometallic Chemistry 1994, 1, 397; Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519; Dalko, P. I. Tetrahedron 1995, 51, 7579.
7. Ho, T.-L. Synthesis 1979, 1; Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; Freeman, F. In Organic Syntheses by Oxidation with Metal Compounds; Mijs, W. J.; de Jonge, C. R. H. I., Eds.; Plenum Press: New York, 1986; Chapter 1; Pons, J.-M; Santelli, M. Tetrahedron 1988, 44, 4295; Rehder, D.; Gailus, H. Trends in Organometallic Chemistry 1994, 1, 397; Iqbal, J.; Bhatia, B.; Nayyar, N. K. Chem. Rev. 1994, 94, 519; Dalko, P. I. Tetrahedron 1995, 51, 7579.
8. Hirao, T. Chem. Rev. 1997, 97, 2707.
9. Scheffold, R In Modern Synthetic Methods, Vol 3; Otto Salle Verlag GmbH: Frankfurt, 1983; Scheffold, R.; Busato, S. Helv. Chim. Acta 1994, 77, 92; Ozaki, S.; Horiguchi, I.; Matsushita, H.; Ohmori, H. Tetrahedron Lett. 1994, 35, 725; Ozaki, S.; Matsui, E.; Waku, J.; Ohmori, H. Tetrahedron Lett. 1997, 38, 2705; Rollin, Y.; Derien, S.; Duñach, E.; Gebehenne, C.; Perichon, J. Tetrahedron 1993, 49, 7723; Mubarak, M. S.; Pagel, M.; Marcus, L. M.; Peters, D. G. J. Org. Chem. 1998, 63, 1319.
10. Scheffold, R In Modern Synthetic Methods, Vol 3; Otto Salle Verlag GmbH: Frankfurt, 1983; Scheffold, R.; Busato, S. Helv. Chim. Acta 1994, 77, 92; Ozaki, S.; Horiguchi, I.; Matsushita, H.; Ohmori, H. Tetrahedron Lett. 1994, 35, 725; Ozaki, S.; Matsui, E.; Waku, J.; Ohmori, H. Tetrahedron Lett. 1997, 38, 2705; Rollin, Y.; Derien, S.; Duñach, E.; Gebehenne, C.; Perichon, J. Tetrahedron 1993, 49, 7723; Mubarak, M. S.; Pagel, M.; Marcus, L. M.; Peters, D. G. J. Org. Chem. 1998, 63, 1319.
11. Scheffold, R In Modern Synthetic Methods, Vol 3; Otto Salle Verlag GmbH: Frankfurt, 1983; Scheffold, R.; Busato, S. Helv. Chim. Acta 1994, 77, 92; Ozaki, S.; Horiguchi, I.; Matsushita, H.; Ohmori, H. Tetrahedron Lett. 1994, 35, 725; Ozaki, S.; Matsui, E.; Waku, J.; Ohmori, H. Tetrahedron Lett. 1997, 38, 2705; Rollin, Y.; Derien, S.; Duñach, E.; Gebehenne, C.; Perichon, J. Tetrahedron 1993, 49, 7723; Mubarak, M. S.; Pagel, M.; Marcus, L. M.; Peters, D. G. J. Org. Chem. 1998, 63, 1319.
12. Scheffold, R In Modern Synthetic Methods, Vol 3; Otto Salle Verlag GmbH: Frankfurt, 1983; Scheffold, R.; Busato, S. Helv. Chim. Acta 1994, 77, 92; Ozaki, S.; Horiguchi, I.; Matsushita, H.; Ohmori, H. Tetrahedron Lett. 1994, 35, 725; Ozaki, S.; Matsui, E.; Waku, J.; Ohmori, H. Tetrahedron Lett. 1997, 38, 2705; Rollin, Y.; Derien, S.; Duñach, E.; Gebehenne, C.; Perichon, J. Tetrahedron 1993, 49, 7723; Mubarak, M. S.; Pagel, M.; Marcus, L. M.; Peters, D. G. J. Org. Chem. 1998, 63, 1319.
13. Scheffold, R In Modern Synthetic Methods, Vol 3; Otto Salle Verlag GmbH: Frankfurt, 1983; Scheffold, R.; Busato, S. Helv. Chim. Acta 1994, 77, 92; Ozaki, S.; Horiguchi, I.; Matsushita, H.; Ohmori, H. Tetrahedron Lett. 1994, 35, 725; Ozaki, S.; Matsui, E.; Waku, J.; Ohmori, H. Tetrahedron Lett. 1997, 38, 2705; Rollin, Y.; Derien, S.; Duñach, E.; Gebehenne, C.; Perichon, J. Tetrahedron 1993, 49, 7723; Mubarak, M. S.; Pagel, M.; Marcus, L. M.; Peters, D. G. J. Org. Chem. 1998, 63, 1319.
14. Scheffold, R In Modern Synthetic Methods, Vol 3; Otto Salle Verlag GmbH: Frankfurt, 1983; Scheffold, R.; Busato, S. Helv. Chim. Acta 1994, 77, 92; Ozaki, S.; Horiguchi, I.; Matsushita, H.; Ohmori, H. Tetrahedron Lett. 1994, 35, 725; Ozaki, S.; Matsui, E.; Waku, J.; Ohmori, H. Tetrahedron Lett. 1997, 38, 2705; Rollin, Y.; Derien, S.; Duñach, E.; Gebehenne, C.; Perichon, J. Tetrahedron 1993, 49, 7723; Mubarak, M. S.; Pagel, M.; Marcus, L. M.; Peters, D. G. J. Org. Chem. 1998, 63, 1319.
15. Hirao, T.; Hirano, K.; Hasegawa, T.; Ikeda, I.; Ohshiro, Y. J. Org. Chem. 1993, 58, 6529.
16. Ogawa, A.; Ohya, S.; Sumino, Y.; Sonoda, N.; Hirao, T. Tetrahedron Lett. 1997, 38, 9017.
17. Tanaka, H.; Sumida, S.-i.; Nishioka, Y.; Kobayashi, N.; Tokumaru, Y.; Kameyama, Y.; Torii, S. J. Org. Chem. 1997, 62, 3610.
18. Lopez, R.; Hays, D. S.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 6949.
19. Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schröder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968.
20. Nicolaou, K. C.; Liu, J.-J.; Yang, Z.; Ueno, H.; Guy, R. K.; Sorensen, E. J.; Claiborne, C. F.; Hwang, C.-K.; Nakada, M.; Nantermet, P. G. J. Am. Chem. Soc. 1995, 117, 634; Shiina, I.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Saitoh, K.; Mukaiyama, T. Chem. Lett. 1997, 419; Kammermeier, B.; Beck, G.; Holla, W.; Jacobi, D.; Napierski, B.; Jendralla, H.; Chem. Eur. J. 1996, 2, 307; Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
21. Nicolaou, K. C.; Liu, J.-J.; Yang, Z.; Ueno, H.; Guy, R. K.; Sorensen, E. J.; Claiborne, C. F.; Hwang, C.-K.; Nakada, M.; Nantermet, P. G. J. Am. Chem. Soc. 1995, 117, 634; Shiina, I.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Saitoh, K.; Mukaiyama, T. Chem. Lett. 1997, 419; Kammermeier, B.; Beck, G.; Holla, W.; Jacobi, D.; Napierski, B.; Jendralla, H.; Chem. Eur. J. 1996, 2, 307; Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
22. Nicolaou, K. C.; Liu, J.-J.; Yang, Z.; Ueno, H.; Guy, R. K.; Sorensen, E. J.; Claiborne, C. F.; Hwang, C.-K.; Nakada, M.; Nantermet, P. G. J. Am. Chem. Soc. 1995, 117, 634; Shiina, I.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Saitoh, K.; Mukaiyama, T. Chem. Lett. 1997, 419; Kammermeier, B.; Beck, G.; Holla, W.; Jacobi, D.; Napierski, B.; Jendralla, H.; Chem. Eur. J. 1996, 2, 307; Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
23. Nicolaou, K. C.; Liu, J.-J.; Yang, Z.; Ueno, H.; Guy, R. K.; Sorensen, E. J.; Claiborne, C. F.; Hwang, C.-K.; Nakada, M.; Nantermet, P. G. J. Am. Chem. Soc. 1995, 117, 634; Shiina, I.; Nishimura, T.; Ohkawa, N.; Sakoh, H.; Nishimura, K.; Saitoh, K.; Mukaiyama, T. Chem. Lett. 1997, 419; Kammermeier, B.; Beck, G.; Holla, W.; Jacobi, D.; Napierski, B.; Jendralla, H.; Chem. Eur. J. 1996, 2, 307; Kammermeier, B.; Beck, G.; Jacobi, D.; Jendralla, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 685.
24. Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014; Park, J.; Pedersen, S. F. J. Org. Chem. 1990, 55, 5924; Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28; Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316.
25. Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014; Park, J.; Pedersen, S. F. J. Org. Chem. 1990, 55, 5924; Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28; Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316.
26. Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014; Park, J.; Pedersen, S. F. J. Org. Chem. 1990, 55, 5924; Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28; Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316.
27. Freudenberger, J. H.; Konradi, A. W.; Pedersen, S. F. J. Am. Chem. Soc. 1989, 111, 8014; Park, J.; Pedersen, S. F. J. Org. Chem. 1990, 55, 5924; Konradi, A. W.; Pedersen, S. F. J. Org. Chem. 1992, 57, 28; Konradi, A. W.; Kemp, S. J.; Pedersen, S. F. J. Am. Chem. Soc. 1994, 116, 1316.
28. Hirao, T.; Hasegawa, T.; Mugurama, Y.; Ikeda, I. J. Org. Chem. 1996, 61, 366; Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. Abstracts for the 6th International Conference on New Aspects of Organic Chemistry, 1994; p 175.
29. Hirao, T.; Hasegawa, T.; Mugurama, Y.; Ikeda, I. J. Org. Chem. 1996, 61, 366; Hirao, T.; Hasegawa, T.; Muguruma, Y.; Ikeda, I. Abstracts for the 6th International Conference on New Aspects of Organic Chemistry, 1994; p 175.
30. Hirao, T.; Asahara, M.; Muguruma, Y.; Ogawa, A. J. Org. Chem. 1998, 62, 4566.
31. Hirao, T.; Hatano, B.; Asahara, M.; Muguruma, Y.; Ogawa, A. Tetrahedron Lett. 1998, 39, 5247.
32. Fürstner, A.; Hupperts, A. J. Am. Chem. Soc. 1995, 117, 4468.
33. Gansäuer, A. Chem. Commun. 1997, 457.
34. Gansäuer, A. Synlett 1997, 363.
35. Lipski, T. A.; Hilfiker, M. A.; Nelson, S. G. J. Org. Chem. 1997, 62, 4566.
36. Gansäuer, A.; Bauer, D. J. Org. Chem. 1998, 63, 2070.
37. Léonard, E.; Duñach, E.; Périchon, J. J. Chem. Soc., Chem. Commun. 1989, 276.
38. Nomura, R.; Matsuno, T.; Endo, T. J. Am. Chem. Soc. 1996, 118, 11666.
39. Svatos, A.; Boland, W. Synlett 1998, 549.
40. Tanaka, H.; Dhimane, H.; Fujita, H.; Ikemoto, Y.; Torii, S. Tetrahedron Lett. 1988, 29, 3811.
41. Tanaka, H.; Nakahara, T.; Dhimane, H.; Torii, S. Synlett 1989, 51.
42. Liao, P.; Huang, Y.; Zhang, Y. Synth. Commun. 1997, 27, 1483.
43. Hatano, B.; Ogawa, A.; Hirao, T. J. Org. Chem. in press.
44. Frainnet, E.; Bourhis, R.; Simonin, F.; Moulines, F. J. Organometal. Chem. 1976, 105, 17.
45. Shimada, H.; Qü. J.-P.; Matsuzaka, M.; Ishii, Y.; Hidai, M. Chem. Lett. 1995, 671.
46. Corey, E. J.; Zheng, G. Z. Tetrahedron Lett. 1997, 38, 2045.
47. Gansäuer, A.; Pierobon, M.; Bluhm, H. Angew. Chem., Int. Ed. 1998, 37, 101.
48. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785; J. Am. Chem. Soc. 1996, 118, 3182.
49. Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1995, 117, 6785; J. Am. Chem. Soc. 1996, 118, 3182.
50. Crowe W. E.; Rachita, M. J. J. Am. Chem. Soc. 1995, 117, 6787.
51. Fürstner A.; Shi, N. J. Am. Chem. Soc. 1996, 118, 12349.
52. Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1997, 38, 6307.
53. Fürstner, A. Chem. Eur. J. 1998, 4, 567.