Rhodium-catalyzed disulfide exchange reaction

Journal of the American Chemical Society

Volumn 125, Issue 22, 2003, Pages 6624-6625

  Arisawa, Mieko ^a   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; FLUOROFORM; PEPTIDE DERIVATIVE; PHOSPHINE DERIVATIVE; RUTHENIUM COMPLEX; SULFONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; DISULFIDE BOND; REACTION ANALYSIS; SYNTHESIS; TECHNIQUE;

CATALYSIS; CYSTINE; DISULFIDES; MESYLATES; PEPTIDES; PHOSPHINES; RHODIUM;

EID: 0038209235     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035221u     Document Type: Article

References (37)

1. Parker, A. J.; Kharasch, N. Chem. Rev. 1959, 59, 583. Also see the following for the metal-catalyzed S-S bond cleavage. Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grutzmacher, H., Eds.: Wiley-VCH: Weinheim, 2001; p 271. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435.
2. Parker, A. J.; Kharasch, N. Chem. Rev. 1959, 59, 583. Also see the following for the metal-catalyzed S-S bond cleavage. Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grutzmacher, H., Eds.: Wiley-VCH: Weinheim, 2001; p 271. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435.
3. Parker, A. J.; Kharasch, N. Chem. Rev. 1959, 59, 583. Also see the following for the metal-catalyzed S-S bond cleavage. Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grutzmacher, H., Eds.: Wiley-VCH: Weinheim, 2001; p 271. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435.
4. Parker, A. J.; Kharasch, N. Chem. Rev. 1959, 59, 583. Also see the following for the metal-catalyzed S-S bond cleavage. Kuniyasu, H. In Catalytic Heterofunctionalization; Togni, A., Grutzmacher, H., Eds.: Wiley-VCH: Weinheim, 2001; p 271. Kondo, T.; Mitsudo, T. Chem. Rev. 2000, 100, 3205. Beletskaya, I.; Moberg, C. Chem. Rev. 1999, 99, 3435.
5. Rosengren, Kj. Acta Chem. Scand. 1962, 16, 1401. Milligan, B.; Rivett, D. E.; Savige, W. E. Aust. J. Chem. 1963, 16, 1020.
6. Rosengren, Kj. Acta Chem. Scand. 1962, 16, 1401. Milligan, B.; Rivett, D. E.; Savige, W. E. Aust. J. Chem. 1963, 16, 1020.
7. Sayamol, K.; Knight, A. R. Can. J. Chem. 1968, 46, 999.
8. 2 is reported, Itoh, T.; Tsutsumi, N.; Ohsawa, A. Bioorg. Med. Chem. Lett. 1999, 9, 2161.
9. 2 is reported, Itoh, T.; Tsutsumi, N.; Ohsawa, A. Bioorg. Med. Chem. Lett. 1999, 9, 2161.
10. 2 is reported, Itoh, T.; Tsutsumi, N.; Ohsawa, A. Bioorg. Med. Chem. Lett. 1999, 9, 2161.
11. 2 is reported, Itoh, T.; Tsutsumi, N.; Ohsawa, A. Bioorg. Med. Chem. Lett. 1999, 9, 2161.
12. Leandri, G.; Tundo, A. Ric. Sci. 1953, 23, 1646: Chem. Abstr. 1954, 48. 12699t.
13. Leandri, G.; Tundo, A. Ric. Sci. 1953, 23, 1646: Chem. Abstr. 1954, 48. 12699t.
14. McAllan, D. T.; Cullum, T. V.; Dean, R. A.; Fidler, F. A. J. Am. Chem. Soc. 1951, 73, 3627. Parker, A. J.; Kharasch, N. J. Am. Chem. Soc. 1960, 82. 3071. Haraldson, L.; Olander, C. J.; Sunner, S.; Varde, E. Acta Chem. Scand. 1960, 14, 1509. Dalman, G.; McDermed, J.; Gorin, G. J. Org. Chem. 1964, 29, 1480. Harpp, D. N.; Smith, R. A. J. Am. Chem. Soc. 1982, 104, 6045.
15. McAllan, D. T.; Cullum, T. V.; Dean, R. A.; Fidler, F. A. J. Am. Chem. Soc. 1951, 73, 3627. Parker, A. J.; Kharasch, N. J. Am. Chem. Soc. 1960, 82. 3071. Haraldson, L.; Olander, C. J.; Sunner, S.; Varde, E. Acta Chem. Scand. 1960, 14, 1509. Dalman, G.; McDermed, J.; Gorin, G. J. Org. Chem. 1964, 29, 1480. Harpp, D. N.; Smith, R. A. J. Am. Chem. Soc. 1982, 104, 6045.
16. McAllan, D. T.; Cullum, T. V.; Dean, R. A.; Fidler, F. A. J. Am. Chem. Soc. 1951, 73, 3627. Parker, A. J.; Kharasch, N. J. Am. Chem. Soc. 1960, 82. 3071. Haraldson, L.; Olander, C. J.; Sunner, S.; Varde, E. Acta Chem. Scand. 1960, 14, 1509. Dalman, G.; McDermed, J.; Gorin, G. J. Org. Chem. 1964, 29, 1480. Harpp, D. N.; Smith, R. A. J. Am. Chem. Soc. 1982, 104, 6045.
17. McAllan, D. T.; Cullum, T. V.; Dean, R. A.; Fidler, F. A. J. Am. Chem. Soc. 1951, 73, 3627. Parker, A. J.; Kharasch, N. J. Am. Chem. Soc. 1960, 82. 3071. Haraldson, L.; Olander, C. J.; Sunner, S.; Varde, E. Acta Chem. Scand. 1960, 14, 1509. Dalman, G.; McDermed, J.; Gorin, G. J. Org. Chem. 1964, 29, 1480. Harpp, D. N.; Smith, R. A. J. Am. Chem. Soc. 1982, 104, 6045.
18. McAllan, D. T.; Cullum, T. V.; Dean, R. A.; Fidler, F. A. J. Am. Chem. Soc. 1951, 73, 3627. Parker, A. J.; Kharasch, N. J. Am. Chem. Soc. 1960, 82. 3071. Haraldson, L.; Olander, C. J.; Sunner, S.; Varde, E. Acta Chem. Scand. 1960, 14, 1509. Dalman, G.; McDermed, J.; Gorin, G. J. Org. Chem. 1964, 29, 1480. Harpp, D. N.; Smith, R. A. J. Am. Chem. Soc. 1982, 104, 6045.
19. Sanger, F. Nature 1953, 171, 1025. Kolthoff, I. M.; Stricks, W.; Kapoor, R. C. J. Am. Chem. Soc. 1955. 77, 4733. Benesch, R. E.; Benesch, R. J. Am. Chem. Soc. 1958, 80, 1666. Ryle, A. P.; Sanger, F.; Smith, L. F.; Kitai, R. Biochem. J. 1955, 60, 541. Kice, J. L.; Ekman, G. E. J. Org. Chem. 1975, 40, 711.
20. Sanger, F. Nature 1953, 171, 1025. Kolthoff, I. M.; Stricks, W.; Kapoor, R. C. J. Am. Chem. Soc. 1955. 77, 4733. Benesch, R. E.; Benesch, R. J. Am. Chem. Soc. 1958, 80, 1666. Ryle, A. P.; Sanger, F.; Smith, L. F.; Kitai, R. Biochem. J. 1955, 60, 541. Kice, J. L.; Ekman, G. E. J. Org. Chem. 1975, 40, 711.
21. Sanger, F. Nature 1953, 171, 1025. Kolthoff, I. M.; Stricks, W.; Kapoor, R. C. J. Am. Chem. Soc. 1955. 77, 4733. Benesch, R. E.; Benesch, R. J. Am. Chem. Soc. 1958, 80, 1666. Ryle, A. P.; Sanger, F.; Smith, L. F.; Kitai, R. Biochem. J. 1955, 60, 541. Kice, J. L.; Ekman, G. E. J. Org. Chem. 1975, 40, 711.
22. Sanger, F. Nature 1953, 171, 1025. Kolthoff, I. M.; Stricks, W.; Kapoor, R. C. J. Am. Chem. Soc. 1955. 77, 4733. Benesch, R. E.; Benesch, R. J. Am. Chem. Soc. 1958, 80, 1666. Ryle, A. P.; Sanger, F.; Smith, L. F.; Kitai, R. Biochem. J. 1955, 60, 541. Kice, J. L.; Ekman, G. E. J. Org. Chem. 1975, 40, 711.
23. Sanger, F. Nature 1953, 171, 1025. Kolthoff, I. M.; Stricks, W.; Kapoor, R. C. J. Am. Chem. Soc. 1955. 77, 4733. Benesch, R. E.; Benesch, R. J. Am. Chem. Soc. 1958, 80, 1666. Ryle, A. P.; Sanger, F.; Smith, L. F.; Kitai, R. Biochem. J. 1955, 60, 541. Kice, J. L.; Ekman, G. E. J. Org. Chem. 1975, 40, 711.
24. Disulfide-thiol exchange reaction was reported. For example, Dalman, G.; McDermed, J.; Gorin, G. J. Org. Chem. 1964, 29, 1480. Eldjarn, L.; Pihl, A. J. Am. Chem. Soc. 1957, 79, 4589.
25. Disulfide-thiol exchange reaction was reported. For example, Dalman, G.; McDermed, J.; Gorin, G. J. Org. Chem. 1964, 29, 1480. Eldjarn, L.; Pihl, A. J. Am. Chem. Soc. 1957, 79, 4589.
26. Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, 343, 27. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 763. Arisawa, M.; Momozuka, R.; Yamaguchi, M. Chem. Lett, 2002, 272. Arisawa, M.; Suwa, A.; Fujimoto, K.; Yamaguchi, M. Adv. Synth. Cat. 2003, 345, 560.
27. Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, 343, 27. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 763. Arisawa, M.; Momozuka, R.; Yamaguchi, M. Chem. Lett, 2002, 272. Arisawa, M.; Suwa, A.; Fujimoto, K.; Yamaguchi, M. Adv. Synth. Cat. 2003, 345, 560.
28. Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, 343, 27. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 763. Arisawa, M.; Momozuka, R.; Yamaguchi, M. Chem. Lett, 2002, 272. Arisawa, M.; Suwa, A.; Fujimoto, K.; Yamaguchi, M. Adv. Synth. Cat. 2003, 345, 560.
29. Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, 343, 27. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 763. Arisawa, M.; Momozuka, R.; Yamaguchi, M. Chem. Lett, 2002, 272. Arisawa, M.; Suwa, A.; Fujimoto, K.; Yamaguchi, M. Adv. Synth. Cat. 2003, 345, 560.
30. Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, 343, 27. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 763. Arisawa, M.; Momozuka, R.; Yamaguchi, M. Chem. Lett, 2002, 272. Arisawa, M.; Suwa, A.; Fujimoto, K.; Yamaguchi, M. Adv. Synth. Cat. 2003, 345, 560.
31. Arisawa, M.; Yamaguchi, M. J. Am. Chem. Soc. 2000, 122, 2387. Arisawa, M.; Yamaguchi, M. Adv. Synth. Cat. 2001, 343, 27. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 311. Arisawa, M.; Yamaguchi, M. Org. Lett. 2001, 3, 763. Arisawa, M.; Momozuka, R.; Yamaguchi, M. Chem. Lett, 2002, 272. Arisawa, M.; Suwa, A.; Fujimoto, K.; Yamaguchi, M. Adv. Synth. Cat. 2003, 345, 560.
32. Examples of selenosulfide synthesis. Nakazaki, M. J. Chem. Soc., Jpn. Pure Chem. Sect. 1954, 75, 338. Kostiner, E. S.; Reddy, M. N.; Urch, D. S.; Massay, A. G. J. Organomet. Chem. 1968, 15, 383. Sister, H. H.; Kotia, N. K, J. Org. Chem. 1971, 36, 1700. Guo, H.; Zhang, Y. J. Chem. Res. 2000, 374. Goto, K.; Nagahama, M.; Mizushima, T.; Shimada, K.; Kawashima, T.; Okazaki, R. Org. Lett. 2001, 3, 3569. Potapov, V. A.; Amosova, S. V.; Petrov, P. A.; Romanenko, L. S.; Keiko, V. V. Sulfur Lett. 1992, 15, 121.
33. Examples of selenosulfide synthesis. Nakazaki, M. J. Chem. Soc., Jpn. Pure Chem. Sect. 1954, 75, 338. Kostiner, E. S.; Reddy, M. N.; Urch, D. S.; Massay, A. G. J. Organomet. Chem. 1968, 15, 383. Sister, H. H.; Kotia, N. K, J. Org. Chem. 1971, 36, 1700. Guo, H.; Zhang, Y. J. Chem. Res. 2000, 374. Goto, K.; Nagahama, M.; Mizushima, T.; Shimada, K.; Kawashima, T.; Okazaki, R. Org. Lett. 2001, 3, 3569. Potapov, V. A.; Amosova, S. V.; Petrov, P. A.; Romanenko, L. S.; Keiko, V. V. Sulfur Lett. 1992, 15, 121.
34. Examples of selenosulfide synthesis. Nakazaki, M. J. Chem. Soc., Jpn. Pure Chem. Sect. 1954, 75, 338. Kostiner, E. S.; Reddy, M. N.; Urch, D. S.; Massay, A. G. J. Organomet. Chem. 1968, 15, 383. Sister, H. H.; Kotia, N. K, J. Org. Chem. 1971, 36, 1700. Guo, H.; Zhang, Y. J. Chem. Res. 2000, 374. Goto, K.; Nagahama, M.; Mizushima, T.; Shimada, K.; Kawashima, T.; Okazaki, R. Org. Lett. 2001, 3, 3569. Potapov, V. A.; Amosova, S. V.; Petrov, P. A.; Romanenko, L. S.; Keiko, V. V. Sulfur Lett. 1992, 15, 121.
35. Examples of selenosulfide synthesis. Nakazaki, M. J. Chem. Soc., Jpn. Pure Chem. Sect. 1954, 75, 338. Kostiner, E. S.; Reddy, M. N.; Urch, D. S.; Massay, A. G. J. Organomet. Chem. 1968, 15, 383. Sister, H. H.; Kotia, N. K, J. Org. Chem. 1971, 36, 1700. Guo, H.; Zhang, Y. J. Chem. Res. 2000, 374. Goto, K.; Nagahama, M.; Mizushima, T.; Shimada, K.; Kawashima, T.; Okazaki, R. Org. Lett. 2001, 3, 3569. Potapov, V. A.; Amosova, S. V.; Petrov, P. A.; Romanenko, L. S.; Keiko, V. V. Sulfur Lett. 1992, 15, 121.
36. Examples of selenosulfide synthesis. Nakazaki, M. J. Chem. Soc., Jpn. Pure Chem. Sect. 1954, 75, 338. Kostiner, E. S.; Reddy, M. N.; Urch, D. S.; Massay, A. G. J. Organomet. Chem. 1968, 15, 383. Sister, H. H.; Kotia, N. K, J. Org. Chem. 1971, 36, 1700. Guo, H.; Zhang, Y. J. Chem. Res. 2000, 374. Goto, K.; Nagahama, M.; Mizushima, T.; Shimada, K.; Kawashima, T.; Okazaki, R. Org. Lett. 2001, 3, 3569. Potapov, V. A.; Amosova, S. V.; Petrov, P. A.; Romanenko, L. S.; Keiko, V. V. Sulfur Lett. 1992, 15, 121.
37. Examples of selenosulfide synthesis. Nakazaki, M. J. Chem. Soc., Jpn. Pure Chem. Sect. 1954, 75, 338. Kostiner, E. S.; Reddy, M. N.; Urch, D. S.; Massay, A. G. J. Organomet. Chem. 1968, 15, 383. Sister, H. H.; Kotia, N. K, J. Org. Chem. 1971, 36, 1700. Guo, H.; Zhang, Y. J. Chem. Res. 2000, 374. Goto, K.; Nagahama, M.; Mizushima, T.; Shimada, K.; Kawashima, T.; Okazaki, R. Org. Lett. 2001, 3, 3569. Potapov, V. A.; Amosova, S. V.; Petrov, P. A.; Romanenko, L. S.; Keiko, V. V. Sulfur Lett. 1992, 15, 121.