Aqueous photo-dimerization using 2-pyridylsilyl group as a removable hydrophilic group

Chemistry Letters

Volumn 33, Issue 5, 2004, Pages 596-597

  Nokami, Toshiki ^a   Itami, Kenichiro ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIDINE DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; BIOTRANSFORMATION; CONCENTRATION PROCESS; DERIVATIZATION; DILUTION; DIMERIZATION; HYDROPHILICITY; PHOTODYNAMICS; REACTION ANALYSIS; SILYLATION; SUBSTITUTION REACTION;

EID: 3242749774     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.596     Document Type: Article

References (26)

1. Reviews: "Organic Synthesis in Water," ed. by P. A. Grieco, Blackie Academic & Professional, London (1998); "Organic Reactions in Aqueous Media," ed. by C.-J. Li and T. H. Chan, Wiley-Interscience, New York (1997).
2. Reviews: "Organic Synthesis in Water," ed. by P. A. Grieco, Blackie Academic & Professional, London (1998); "Organic Reactions in Aqueous Media," ed. by C.-J. Li and T. H. Chan, Wiley-Interscience, New York (1997).
3. The use of sugar moiety as a removable hydrophilic group: A. Lubineau and Y. Queneau, J. Org. Chem., 52, 1001 (1987); A. Lubineau and Y. Queneau, Tetrahedron, 45, 6697 (1989).
4. The use of sugar moiety as a removable hydrophilic group: A. Lubineau and Y. Queneau, J. Org. Chem., 52, 1001 (1987); A. Lubineau and Y. Queneau, Tetrahedron, 45, 6697 (1989).
5. Review: K. Itami and J. Yoshida, Chem. Rec., 2, 213 (2002).
6. K. Itami, T. Nokami, and J. Yoshida, Angew. Chem., Int. Ed., 40, 1074 (2001); K. Itami, T. Nokami, and J. Yoshida, Adv. Synth. Catal., 344, 441 (2002).
7. K. Itami, T. Nokami, and J. Yoshida, Angew. Chem., Int. Ed., 40, 1074 (2001); K. Itami, T. Nokami, and J. Yoshida, Adv. Synth. Catal., 344, 441 (2002).
8. R. Kleopfer and H. Morrison, J. Am. Chem. Soc., 94, 255 (1972).
9. M. S. Syamala and V. Ramamurthy, J. Org. Chem., 51, 3712 (1986); V. Ramamurthy, Tetrahedron, 42, 5753 (1986); Solvent effects on the product ratio of photo-dimerization were investigated: Y. Ito, T. Kajita, K. Kunimoto, and T. Matsuura, J. Org. Chem., 54, 587 (1989); Controlled photochemical [2 + 2] cycloadditions were reported: J.-M. Park, W. Zhang, Y. Nakatsuji, T. Majima, and I. Ikeda, Chem. Lett., 1999, 1309; D. M. Bassni, X. Sallenave, V. Darcos, and J.-P. Desvergne, Chem. Commun., 2001, 1446.
10. M. S. Syamala and V. Ramamurthy, J. Org. Chem., 51, 3712 (1986); V. Ramamurthy, Tetrahedron, 42, 5753 (1986); Solvent effects on the product ratio of photo-dimerization were investigated: Y. Ito, T. Kajita, K. Kunimoto, and T. Matsuura, J. Org. Chem., 54, 587 (1989); Controlled photochemical [2 + 2] cycloadditions were reported: J.-M. Park, W. Zhang, Y. Nakatsuji, T. Majima, and I. Ikeda, Chem. Lett., 1999, 1309; D. M. Bassni, X. Sallenave, V. Darcos, and J.-P. Desvergne, Chem. Commun., 2001, 1446.
11. M. S. Syamala and V. Ramamurthy, J. Org. Chem., 51, 3712 (1986); V. Ramamurthy, Tetrahedron, 42, 5753 (1986); Solvent effects on the product ratio of photo-dimerization were investigated: Y. Ito, T. Kajita, K. Kunimoto, and T. Matsuura, J. Org. Chem., 54, 587 (1989); Controlled photochemical [2 + 2] cycloadditions were reported: J.-M. Park, W. Zhang, Y. Nakatsuji, T. Majima, and I. Ikeda, Chem. Lett., 1999, 1309; D. M. Bassni, X. Sallenave, V. Darcos, and J.-P. Desvergne, Chem. Commun., 2001, 1446.
12. M. S. Syamala and V. Ramamurthy, J. Org. Chem., 51, 3712 (1986); V. Ramamurthy, Tetrahedron, 42, 5753 (1986); Solvent effects on the product ratio of photo-dimerization were investigated: Y. Ito, T. Kajita, K. Kunimoto, and T. Matsuura, J. Org. Chem., 54, 587 (1989); Controlled photochemical [2 + 2] cycloadditions were reported: J.-M. Park, W. Zhang, Y. Nakatsuji, T. Majima, and I. Ikeda, Chem. Lett., 1999, 1309; D. M. Bassni, X. Sallenave, V. Darcos, and J.-P. Desvergne, Chem. Commun., 2001, 1446.
13. M. S. Syamala and V. Ramamurthy, J. Org. Chem., 51, 3712 (1986); V. Ramamurthy, Tetrahedron, 42, 5753 (1986); Solvent effects on the product ratio of photo-dimerization were investigated: Y. Ito, T. Kajita, K. Kunimoto, and T. Matsuura, J. Org. Chem., 54, 587 (1989); Controlled photochemical [2 + 2] cycloadditions were reported: J.-M. Park, W. Zhang, Y. Nakatsuji, T. Majima, and I. Ikeda, Chem. Lett., 1999, 1309; D. M. Bassni, X. Sallenave, V. Darcos, and J.-P. Desvergne, Chem. Commun., 2001, 1446.
14. K. Itami, K. Mitsudo, T. Kamei, T. Koike, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 122, 12013 (2000).
15. 3 ligand in the Mizoroki-Heck reaction: A. F. Littke and G. C. Fu, J. Am. Chem. Soc., 123, 6989 (2001).
16. 2Si-substituted molecules soluble in water. The application of this procedure to stilbene derivatives 2 gave rise to homogeneous emulsion, which was used for aqueous photodimerization.
17. H. Schechter, W. J. Link, and G. V. D. Tiers, J. Am. Chem. Soc., 85, 1601 (1963);
18. H. Ulrich, D. V. Rao, F. A. Stuber, and A. A. R. Sayigh, J. Org. Chem., 35, 1121 (1970); D. A. Ben-Efraim and B. S. Green, Tetrahedron, 30, 2357 (1974); K. S. S. P. Rao, S. M. Hubig, J. N. Moorthy, and J. K. Kochi, J. Org. Chem., 64, 8098 (1999).
19. H. Ulrich, D. V. Rao, F. A. Stuber, and A. A. R. Sayigh, J. Org. Chem., 35, 1121 (1970); D. A. Ben-Efraim and B. S. Green, Tetrahedron, 30, 2357 (1974); K. S. S. P. Rao, S. M. Hubig, J. N. Moorthy, and J. K. Kochi, J. Org. Chem., 64, 8098 (1999).
20. H. Ulrich, D. V. Rao, F. A. Stuber, and A. A. R. Sayigh, J. Org. Chem., 35, 1121 (1970); D. A. Ben-Efraim and B. S. Green, Tetrahedron, 30, 2357 (1974); K. S. S. P. Rao, S. M. Hubig, J. N. Moorthy, and J. K. Kochi, J. Org. Chem., 64, 8098 (1999).
21. 2Si-substituted 1,3-dienes, large molecular aggregates were observed. These large aggregates probably stem from nonordered structures as stated in reference 4.
22. T. Hiyama, in "Metal-catalyzed cross-coupling reactions," ed. by F. Diederich and P. J. Stang, Wiley-VCH, Weinheim (1998), Chap. 10; K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); S. E. Denmark and R. F. Sweis, Acc. Chem. Res., 35, 835 (2002).
23. T. Hiyama, in "Metal-catalyzed cross-coupling reactions," ed. by F. Diederich and P. J. Stang, Wiley-VCH, Weinheim (1998), Chap. 10; K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); S. E. Denmark and R. F. Sweis, Acc. Chem. Res., 35, 835 (2002).
24. T. Hiyama, in "Metal-catalyzed cross-coupling reactions," ed. by F. Diederich and P. J. Stang, Wiley-VCH, Weinheim (1998), Chap. 10; K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); S. E. Denmark and R. F. Sweis, Acc. Chem. Res., 35, 835 (2002).
25. T. Hiyama, in "Metal-catalyzed cross-coupling reactions," ed. by F. Diederich and P. J. Stang, Wiley-VCH, Weinheim (1998), Chap. 10; K. Itami, T. Nokami, and J. Yoshida, J. Am. Chem. Soc., 123, 5600 (2001); K. Itami, T. Nokami, Y. Ishimura, K. Mitsudo, T. Kamei, and J. Yoshida, J. Am. Chem. Soc., 123, 11577 (2001); S. E. Denmark and R. F. Sweis, Acc. Chem. Res., 35, 835 (2002).
26. 6 793.3529, found 793.3528.