Fast Tin-Free Hydrodehalogenation and Reductive Radical Cyclization Reactions: A New Reduction Process

Journal of Organic Chemistry

Volumn 69, Issue 6, 2004, Pages 2037-2041

  Vaillard, Santiago E ^a   Postigo, Al ^a   Rossi, Roberto A ^a  

^a DEPARTAMENTO DE FISICOQUÍMICA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; DIFFUSION; REDUCTION;

CYCLIZATION REACTIONS; PHOTOSTIMULATED REACTIONS;

HALOGENATION;

1 ALLYLOXY 2 BROMOBENZENE; 1 ALLYLOXY 2 CHLOROBENZENE; 2 ALLYLOXY 1 BROMONAPHTHALENE; 2 ALLYLOXY 1 CHLORONAPHTHALENE; 3 METHYL 2,3 DIHYDROBENZOFURAN; ACETONE; ANILINE DERIVATIVE; BENZENE DERIVATIVE; BENZOFURAN DERIVATIVE; DIALLYL(2 BROMOPHENYL)AMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CYCLIZATION; DEHALOGENATION; PHOTOCHEMISTRY; PHOTOSTIMULATION; REDUCTION;

EID: 1642348801     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo035477i     Document Type: Article

References (46)

1. (a) Radicals in Organic Synthesis, Vol. 1 and 2; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001.
2. (b) Giese, B.; Göbel, T.; Dickhaut, G.; Thoma, G.; Kulicke, K. J.; Trach, F. In Organic Reactions; Paquette, L., Beak, P., Engelbert, C., Curran, D., Czarnik, A., Scott, E., Hegedus, L., Kelly, R., Overman, L., Roush, W., Smith, A., White, J., Eds.; Wiley & Sons: New York, 1996; pp 301-856.
3. (c) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon: Oxford, U.K., 1986.
4. For a recent review, see Studer, A.; Amrein, S. Synthesis 2002, 7, 835-849.
5. Chatgilialoglu, C.; Dickhaut, J.; Giese, B. J. Org. Chem. 1991, 56, 6399-6403.
6. For reviews on rate constant of different silyl radicals, see (a) Chatgilialoglu, C. Chem. Rev. 1995, 95, 1229-1251.
7. (b) Chatgilialoglu, C.; Newcomb, M. Adv. Organomet. Chem. 1999, 44, 67-112.
8. (a) Chatgilialoglu, C.; Ballestri M. Organometallics 1999, 18, 2395-2397.
9. (b) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Bull. Chem. Soc. Jpn. 2001, 74, 747-752
10. (a) Studer, A.; Amrein, S. Angew. Chem., Int. Ed. 2000, 39, 3080-3082.
11. (b) Studer, A.; Amrein, S.; Schlet, F.; Schulte, T.; Walton, J. J. Am. Chem. Soc. 2003, 125 (19), 5726-5733
12. (a) Roy, S. C.; Guin, C.; Rana, K. K.; Maiti, G. Tetrahedron 2002, 58, 2435-2439.
13. (b) Gonzalez Martin, C.; Murphy, J.; Smith, C. Tetrahedron Lett. 2000, 41, 1833-1836.
14. (c) Yorimitsu, H.; Shinokubo, H.; Oshima, K. Chem. Lett. 2000, 104-106.
15. Boisvert, G.; Giasson, R. Tetrahedron Lett. 1992, 33, 6587-6590.
16. (a) Bunnett, J. F. Acc. Chem. Res. 1992, 25, 2-9.
17. (b) Tomaselli, G. A.; Bunnett, J. F. J. Org. Chem. 1992, 57, 2710-2716.
18. (c) Tomaselli, G. A.; Ciu, J.; Chen, Q.; Bunnett, J. F. J. Chem. Soc., Perkin Trans. 2. 1992, 9-15.
19. (d) Amatore, C.; Badoz-Lambling, J.; Bonnel-Huyghes, C.; Pinson, J.; Savéant, J. M.; Thiébault, A. J. Am. Chem. Soc. 1982, 104, 1979-1986.
20. (a) Beckwith, A. L. J.; Gerba, W. B. J. Chem. Soc., Perkin Trans. 2 1975, 593-600.
21. (b) Beckwith, A. L. J. Tetrahedron 1981, 37, 3073-3099.
22. (c) Beckwith, A. L. J.; Gerba, S. Aust. J. Chem. 1992, 45, 289-308.
23. (d) Annunziata, A.; Galli, C.; Marinelli, M.; Pau, T. Eur. J. Org. Chem. 2001, 1323-1329.
24. Some representative examples can be found in (a) Beckwith, A. L. J.; Abeywikrema, A. N. Tetrahedron Lett. 1986, 27, 109-112.
25. (b) Dittami, J. P.; Ramanathan, H. Tetrahedron Lett. 1988, 29, 45-48.
26. (a) Patel, V. F.; Pattenden, G.; Russel, J. J. Tetrahedron Lett. 1986, 27, 2303-2306.
27. (b) Meijs, G. F.; Beckwith, A. L. J. J. Am. Chem. Soc. 1986, 108, 5890-5893.
28. (c) Beckwith, A. L. J.; Meijs, G. F. J. Org. Chem. 1987, 52, 1922-1930.
29. (d) Togo, H.; Kikuchi, O. Tetrahedron Lett. 1988, 29, 4133-4134.
30. (e) Petrillo, G.; Novi, M.; Garbarino, G.; Filiberti, M. Tetrahedron Lett. 1988, 29, 4185-4188.
31. (f) Beckwith, A. L. J.; Jackson, R. A.; Longmore, R. W. Aust. J. Chem. 1992, 45, 857-863.
32. (g) Amatore, C.; Gareil, M.; Oturan, M. A.; Pinson, J.; Savéant, J. M.; Thiébault, A. J. Org. Chem. 1986, 51, 3757-3761.
33. Vaillard, S. E.; Postigo, A.; Rossi, R. A. J. Org. Chem. 2002, 67, 8500-8506.
34. It is known that acetone enolate anions do not react with primary alkyl radicals but enable the initiation of the photostimulated reaction; see (a) Borosky, G. L.; Pierini, A. B.; Rossi, R. A. J. Org. Chem. 1990, 55, 3705-3707.
35. (b) Rossi, R. A.; Pierini, A. B.; Borosky, G. L. J. Chem. Soc., Perkin Trans. 2. 1994, 2577-2581.
36. (c) Peñéñory, A. B.; Rossi, R. A. Gazz. Chim. Ital. 1995, 125, 605-609.
37. (d) Lukach, A. E.; Rossi, R. A. J. Org. Chem. 1999, 64, 5826-5831.
38. Rossi, R. A.; Pierini, A. B.; Peñéñory, A. B. Chem. Rev. 2003, 103, 71-167.
39. (a) Bordwell, F. G.; Zhang, X. Acc. Chem. Res. 1993, 26, 510-517.
40. (b) Bordwell, F. G.; Zhang, X.; Filler, R. J. Org. Chem. 1993, 58, 6067-6071.
41. Amatore, C.; Oturan, M.; Pinson, J.; Savéant, J. M.; Thiébault, A. J. Am. Chem. Soc. 1985, 107, 3451-3459.
42. Bunnett, J. F.; Creary, X. J. Org. Chem. 1974, 39, 3173-3174.
43. Boisvert, G.; Giasson, R. Tetrahedron Lett. 1992, 33, 6587-6590.
44. Olivero, S.; Duñach, E. Eur. J. Org. Chem. 1999, 64, 1885-1891.
45. Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1996, 61, 2594-2595.
46. Abeywickrema, A. N.; Beckwith, A. L. J.; Gerba, S. J. Org. Chem. 1987, 52, 4072-4078.