Design of polyaromatic hydrocarbon-supported tin reagents: A new family of tin reagents easily removable from reaction mixtures

Journal of Organic Chemistry

Volumn 69, Issue 13, 2004, Pages 4464-4470

  Stien, Didier ^a,b   Gastaldi, Stéphane ^c  

^a CNRS   (France)

^b UNIVERSITÉ DE MONTPELLIER   (France)

^c AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATED CARBON; DERIVATIVES; REDUCTION; REMOVAL; TIN;

ALLYLATION REACTION; CYCLIZATIONS;

POLYCYCLIC AROMATIC HYDROCARBONS;

ACTIVATED CARBON; CATION; POLYCYCLIC AROMATIC HYDROCARBON; PYRENE; RADICAL; REAGENT; TIN; TRIBUTYLTIN;

ALLYLATION; ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CYCLIZATION; ISOLATION PROCEDURE; REDUCTION;

EID: 3042825501     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049868o     Document Type: Article

References (51)

1. Studer, A.; Amreim, S. Synthesis 2002, 835-849.
2. Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem. Soc., Perkin Trans. 1 2000, 3815-4195. See pp 3896-3897 for a list of known polymer supported tin hydrides.
3. Weinshenker, N. M.; Crosby, G. A.; Wong, J. Y. J. Org. Chem. 1975, 40, 1966-1971.
4. Schumann, H.; Pachaly, B. Angew. Chem., Int. Ed. Engl. 1981, 20, 1043-1044.
5. Ueno, Y.; Chino, K.; Watanabe, M.; Moriya, O.; Okawara, M. J. Am. Chem. Soc. 1982, 104, 5564-5566.
6. Gerick, U.; Gerlach, M.; Neumann, W. P.; Vieler, R.; Weintritt, V. Synthesis 1990, 448-452.
7. Blanton, J. R.; Salley, J. M. J. Org, Chem. 1991, 56, 490-491.
8. Neumann, W. P.; Peterseim, M. Synlett 1992, 801-802.
9. Ruel, G.; The, N. K.; Dumartin, G.; Delmond, B.; Pereyre, M. J. Organomet. Chem. 1993, 444, C18-C20.
10. Dumartin, G.; Ruel, G.; Kharboutli, J.; Delmond, B.; Connil, M.-F.; Jousseaume, B.; Pereyre, M. Synlett 1994, 952-954.
11. Dumartin, G.; Pourcel, M.; Delmond, B.; Donard, O.; Pereyre, M. Tetrahedron Lett. 1998, 39, 4663-4666.
12. Chemin, A.; Deleuze, H.; Maillard, B. Eur. Polym. J. 1998, 34 1395-1404.
13. Boussaguet, P.; Delmond, B.; Dumartin, G.; Pereyre, M. Tetrahedron Lett. 2000, 41, 3377-3380.
14. Light, J.; Breslow, R. Tetrahedron Lett. 1990, 31, 2957-2958.
15. Light, J.; Breslow, R. Org. Synth. 1993, 72, 199-207.
16. Han, X.; Hartmann, G. A.; Brazzale, A.; Gaston, R. D. Tetrahedron Lett. 2001, 42, 5837-5839.
17. Vedejs, E.; Duncan, S. M.; Haight, A. R. J. Org. Chem. 1993, 58, 3046-3050.
18. Suga, S.; Manabe, T.; Yoshida, J.-i. Chem. Commun. 1999, 1237-1238.
19. Rai, R.; Collum, D. B. Tetrahedron Lett. 1994, 35, 6221-6224.
20. Clive, D. L. J.; Yang, W. J. Org. Chem. 1995, 60, 2607-2609.
21. Clive, D. L. J.; Wang, J. J. Org. Chem. 2002, 67, 1192-1198.
22. Bergbreiter, D. E.; Walker, S. A. J. Org. Chem. 1989, 54, 5138-5141.
23. Enholm, E. J.; Schulte, J. P. Org. Lett. 1999, 1, 1275-1277.
24. Curran, D. P.; Hadida, S.; Kim, S.-Y.; Luo, Z. J. Am. Chem. Soc. 1999, 121, 6607-6615 and references therein. See also: http:// fluorous.com/tin.html.
25. For a preliminary communication, see: Gastaldi, S.; Stien, D. Tetrahedron Lett. 2002, 43, 4309-4311.
26. Ramage, R.; Raphy, G. Tetrahedron Lett. 1992, 33, 385-388.
27. Brown, A. R.; Irving, S. L.; Ramage, R. Tetrahedron Lett. 1993, 34, 7129-7132.
28. Ramage, R.; Wahl, F. O. Tetrahedron Lett. 1993, 34, 7133-7136.
29. Brown, A. R.; Irving, S. L.; Ramage, R.; Raphy, G. Tetrahedron 1995, 51, 11815-11830.
30. Hay, A. M.; Hobbs-Dewitt, S.; MacDonald, A. A.; Ramage, R. Synthesis 1999, 1979-1985.
31. Neumann, W. P.; Pedain, J. Tetrahedron Lett. 1964, 2461-2465.
32. Lautens, M.; Kumanovic, S.; Meyer, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 1329-1330.
33. Connil, M.-F.; Jousseaume, B.; Noiret, N.; Pereyre, M. Organometallics 1994, 13, 24-25.
34. Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404-5406.
35. Chen, R. J.; Zhang, Y. G.; Wang, D.; Dai, H. J. Am. Chem. Soc. 2001, 123, 3838.
36. Gómez, F. J.; Chen, R. J.; Wang, D.; Waymouth, R. M.; Dai, H. Chem. Commun. 2003, 190-191.
37. Petrov, P.; Stassin, F.; Pagnoulle, C.; Jérôme, R. Chem. Commun. 2003, 2904-2905.
38. Katz, E. J. Electroanal. Chem. 1994, 365, 157.
39. Jaegfeldt, H.; Kuwana, T.; Johansson, G. J. Am. Chem. Soc. 1983, 105, 1805.
40. Warmus, J. S.; Da Silva, M. I. Org. Lett. 2000, 2, 1807-1809.
41. Neumann, W. P.; Hillgärtner, H.; Baines, K.; Dicke, R.; Vorspohl, K.; Kobs, U.; Nussbeutel, U. Tetrahedron 1989, 45, 951.
42. Brix, B.; Clark, T. J. Org. Chem. 1988, 53, 3365.
43. Leutenegger, U.; Madin, A.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1989, 28, 60-61.
44. Still, J. C. J. Am. Chem. Soc. 1977, 99, 4836-4838.
45. Stork, G,; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303-304.
46. Chatgilialoglu, C.; Newcomb, M. Adv. Organomet. Chem. 1999, 99, 90-99.
47. Rosenstein I. J. In Radicals in Organic Synthesis Vol. 1; Renaud, P. and Sibi, M. P., Eds.; Wiley -VCH: New York, 2001; pp 50-69.
48. Marshall, J. A. in Organometallics in Synthesis A Manual; Schlosser M., Ed.; John Wiley & Sons: New York, 2002; pp 355-464.
49. Sinistera, J. V.; Mouloungui, Z.; Delmas, M.; Gasset, A. Synthesis 1985, 1097-1100.
50. Hayashi, K.; Maruyama, T.; Yachi, T.; Kudo, K.; Ichimura, K. J. Chem. Soc., Perkin Trans. 2 1998, 981-987.
51. Yang, N.-C. C.; Minsek, D. W.; Johnson, D. G.; Larson, J. R.; Petrich, J. W. Tetrahedron 1989, 45, 4669-4682.