Stoichiometric and catalytic activation of the α- and β-2,3,4-tri-O-acetyl-5-thioxylopyranosyl bromide inside the cavity of the Pd3(dppm)3(CO)2+ cluster

Inorganic Chemistry

Volumn 42, Issue 16, 2003, Pages 4909-4917

  Brevet, David ^a   Mugnier, Yves ^a   Lemaître, Frédéric ^a,c   Lucas, Dominique ^a   Samreth, Soth ^b   Harvey, Pierre D ^c  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b Laboratoires Fournier   (France)

^c UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA 2,3,4 TRI O ACETYL 5 THIOXYLOPYRANOSYL BROMIDE; BETA 2,3,4 TRI O ACETYL 5 THIOXYLOPYRANOSYL BROMIDE; BROMINE DERIVATIVE; PALLADIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; ELECTROCHEMISTRY; LOW TEMPERATURE; REACTION ANALYSIS; STOICHIOMETRY;

EID: 0043032956     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic026279x     Document Type: Article

References (71)

1. (a) Kulawiec, R. J.; Crabtree, R. H. Coord. Chem. Rev. 1990, 99, 89.
2. (b) Stille, J. K.; Kriesler, S. Y. L. Acc. Chem. Res. 1977, 10, 434.
3. (b) Organometallic Mechanisms and Catalysis; Kochi, J. K., Ed.; Academic Press: New York, 1978; p 156.
4. (c) Comprehensive Organometallic Chemistry, II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, U.K.; 1995; Vol.12, p 161.
5. (d) Principles and Applications of Organotransition Metal Chemistry; Collman, J. P., Hegedus, L. S., Norton, J. R., Eds.; University Science Books: Mill Valley, CA, 1987.
6. (e) Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Hermann, W. A., Eds.; Wiley: Weinheim, Germany, 1999.
7. (f) Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis: Tsuji, J., Ed.; Wiley: Chichester, U.K., 2000.
8. (g) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009 and references therein.
9. Brevet, D.; Lucas, D.; Cattey, H.; Lemaître, F.; Mugnier, Y.; Harvey, P. D. J. Am. Chem. Soc. 2001, 123, 4340.
10. Lemaître, F.; Brevet, D.; Lucas, D.; Vallat, A.; Mugnier, Y.; Harvey, P. D. Inorg. Chem. 2002, 41, 2368.
11. (a) Garegg, P. J. Adv. Carbohyd. Res. Bi. 1997, 52, 179.
12. (b) Toshima, K.; Tatsuta K. Chem. Rev. 1993, 93, 1503.
13. (a) Only a few electrosyntheses of glycoside have been described and concern the O-glycosylation reaction starting from S-glycoside or glycosyl halide or glycosyl alkoxides as glycoside acceptor. Recently, efficient electrochemical N-glycosylation has been reported.
14. (b) Balavoine, G.; Gref, A.; Fischer, J. C.; Lubineau, A. Tetrahedron Lett. 1998, 40, 5761.
15. (c) Amatore, C.; Jutand, A.; Mallet, J. M.; Meyer, G.; Sinay, P. J. Chem. Soc., Chem. Commun. 1990, 718.
16. (d) Mallet, J. M.; Gilbert, G.; Yvelin, F.; Jutand, A.; Amatore, C.; Sinay, P. Carbohydr. Res. 1993, 244, 237.
17. (e) Amatore, C.; Jutand, A.; Meyer, G.; Bourhis, P.; Machetto, F.; Mallet, J. M.; Sinay, P.; Tabeur, C.; Zhang, Y. M. J. Appl. Electrochem. 1994, 24, 725.
18. (f) Balavoine, G.; Berteina, S.; Gref, A.; Fischer, J. C.; Lubineau, A. J. Carbohydr. Chem. 1995, 14, 1217.
19. (g) Rondini, S.; Mussini, P. R.; Sello, G.; Vismara, E. J. Electrochem. Soc. 1998, 145, 1108.
20. (h) Noyori, R.; Kirimoto, I. J. Org. Chem. 1986, 51, 4320.
21. (i) Nokami, J.; Osafune, M.; Ito, Y; Miyake, F.; Sumida, S. I.; Torii, S. Chem. Lett. 1999, 1053.
22. (a) Research in this area is intensive because its derivatives belong to a class of compounds called α-D-xylopyranosides, some of which present oral antithrombotic activity.
23. (b) Horton, D.; Wander, J. D. In The Carbohydrates Chemistry, and Biochemistry; Pigman, W., Horton, D., Eds.; Academic: New York, 1980; Vol. IB, p 799.
24. (c) Bellamy, F.; Horton, D.; Pacart, F.; Millet, J.; Samreth, S.; Chazan, J. B. J. Med. Chem. 1993, 36, 898.
25. (d) Samreth, S.; Bellamy, F.; Millet, J.; Barberousse, V.; Renault, P.; Bajgrowick, J. EPO, 365397, 1991; Chem. Abstr. 1991, 114, 122964k.
26. (d) Samreth, S.; Bellamy, F.; Millet, J.; Barberousse, V.; Renault, P.; Bajgrowick, J. EPO, 365397, 1991; Chem. Abstr. 1991, 114, 122964k.
27. (e) Barberousse, V.; Legendre, C.; Samreth, S.; Edgar, A. U.S. Patent 6291433, 2001.
28. (a) Manojlovic-Muir, L. J.; Muir, K. W.; Lloyd, B. R.; Puddephatt, R. J. J. Chem. Soc., Chem. Commun. 1983, 1336.
29. (b) Lloyd, B. R.; Puddephatt, R. J. Inorg. Chim. Acta 1984, 90, L77.
30. (a) Whistler, R. L.; Van Es, T. J. Org. Chem. 1963, 28, 2303.
31. (b) Baudry, M.; Bouchu, M. N.; Descotes, G.; Praly, J. P.; Bellamy, F. Carbohydr. Res. 1996, 282, 237.
32. Provencher, R.; Aye, K. T.; Drouin, M.; Gagnon, J.; Boudreault, N.; Harvey, P. D. Inorg. Chem. 1994, 33, 3689.
33. Bozo, E.; Boros, S.; Kunszmann, J. Carbohydr. Res. 1997. 299, 59.
34. Gautheron, I.; Mugnier, Y.; Hierso, K.; Harvey, P. D. Can. J. Chem. 1997, 75, 1182.
35. Wave E′ exhibits a similar intensity as A, suggesting a single 2-electron process as well.
36. (a) Manojlovic-Muir, L. J.; Muir, K. W.; Lloyd, B. R.; Puddephatt, R. J. J. Chem. Soc., Chem. Commun. 1985, 536.
37. (b) Lloyd, B. R.; Manojlovic-Muir, L. J.; Muir, K. W.; Puddephatt, R. J. Organometallics 1993, 12, 1231.
38. Harvey, P. D.; Hierso, K.; Braunstein, P.; Morise, X. Inorg. Chem. Acta 1996, 250, 337.
39. +" is assumed to evolve, but no attempt was made to identify the organic products due to the small amount used in stoichiometric conditions, and in the presence of a large excess of supporting electrolyte.
40. +" is stabilized by resonance involving delocalization of the S atom lone pair.
41. The demonstration for eqs 10-14 is provided in the Supporting Information.
42. Basic Inorganic Chemistry; Cotton, F. A., Wilkinson, G., Eds.; John Wiley & Sons: New York, 1980; p 61.
43. Harvey, P. D.; Provencher, R.; Gagnon, J.; Zhang, T.; Fortin, D.; Hierso, K.; Drouin, M.; Socol, S. M. Can. J. Chem. 1996, 74, 2268.
44. 2).
45. (b) Zhang, T.; Drouin, M.; Harvey, P. D. J. Chem. Soc., Chem. Commun. 1996, 877.
46. 2+⋯Br-Xyl exists.
47. Brevet, D. Ph.D. Thesis, Université de Bourgogne, Dijon, France, 2002.
48. β-Xyl-Br is slightly unstable in solution, so long term electrochemical experiments are altered by this instability.
49. The product is EPR silent.
50. 2O. The products were separated and isolated by column chromatography on silica gel. The overall isolated yield is 91%.
51. Peters, D. G. In Organic Electrochemistry, 3rd ed., revised and expanded; Lund, H., Baiser, M. M., Dekker, M., Eds.; INC: New York, 1992; p 361.
52. Nishino, T.; Watanabe T.; Okada, M.; Nishiyama, Y.; Sonoda, N. J. Org. Chem. 2002, 67, 966.
53. (a) Organic Chemistry of Stable Free Radicals; Forrester, A. R., Hay, J. M., Thomson, R. H., Eds.; Academic Press: London, 1968.
54. (b) Rozantsev, E. G. In Free Nitroxyl Radicals; Ulrich, H., Ed.; Plenum Press: New York, 1970.
55. (c) Spin Labeling. Theory and Application; Berliner, L. J., Ed.; Academic Press: New York, 1976.
56. (d) Yamago, S.; Miyazoe, H.; Yoshida, J. Tetrahedron Lett. 1999, 40, 2339.
57. Rota, C.; Barr, D. P.; Martin, M. V.; Guengerich, F. P.; Tomasi, A.; Mason, R. P. Biochem. J. 1997, 328, 565.
58. Witting, P. K.; Travascio, P.; Sen, D.; Mauk, A. G. Inorg. Chem. 2001, 40, 5017.
59. (a) The importance of radical reactions in organic synthesis has recently increased, since functional group conversion of organic compounds under mild conditions is critical for the preparation of natural products and fine chemicals. In particular, the coupling reaction of a sugar anomeric radical with electron poor heteroaromatic bases is effective for the synthesis of C-nucleosides. The addition of glycoside radicals to α,β-unsaturated carbonyl compounds has been developed by Giese et al. as a practical method for the synthesis of C-glycosides.
60. (b) Free Radicals in Organic Chemistry; Fossey, J., Lefort, D., Sorba, J., Eds.; John Wiley & Sons: Paris, 1995.
61. (c) Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Giese, B., Ed.; Pergamon Press: Oxford, 1986.
62. (d) Free Radical Chain Reactions in Organic Synthesis; Motherwell, W. B., Crich, D., Ed.; Academic Press: New York, 1992.
63. (e) Togo, H.; Fujii, M.; Ikuma, T.; Yokoyama, M. Tetrahedron Lett. 1991, 32, 3377.
64. (f) Togo, H.; Ishigami, S., Yokoyama, M. Chem. Lett. 1992, 1673.
65. (g) Togo, H.; Ishigami, S.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1994, 2407.
66. (h) Togo, H.; Ishigami, S.; Fujii, M.; Ikuma, T. Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1994, 2931.
67. (i) For a review see: Giese, B. Angew. Chem., Int. Ed. Engl. 1989, 28, 969.
68. (a) The side products were observed.
69. (b) Maran, F.; Vianello, E.; Catelani, G.; D'Angeli, F. Electrochim. Acta 1989, 34, 587.
70. Brevet, D.; Mugnier, Y.; Samreth, S. Submitted for publication.
71. -.