Intramolecular aryl migration from tin to carbon via a radical atom-transfer process

Organic Letters

Volumn 2, Issue 13, 2000, Pages 1899-1901

  Wakabayashi, Katsuyu ^a   Yorimitsu, Hideki ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001163249     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005971y     Document Type: Article

References (36)

1. (a) Tiecco, M. Acc. Chem. Res. 1980, 13, 51.
2. (b) Fossey, J.; Lefort, D.; Sorba, J. Free Radicals in Organic Chemistry; Wiley: New York, 1995; Chapter 14.
3. (a) Wilt, J. W.; Dockus, C. F. J. Am. Chem. Soc. 1970, 92, 5813.
4. (b) Wilt, J. W.; Chwang, W. K. J. Am. Chem. Soc. 1974, 96, 6194.
5. (c) Wilt, J. W.; Chwang, W. K.; Dockus, C. F.; Tomink, N. M. J. Am. Chem. Soc. 1978, 100, 5534.
6. (d) Sakurai, H.; Hosomi, A. J. Am. Chem. Soc. 1970, 92, 7507.
7. (e) Studer, A.; Bossart, M.; Steen, H. Tetrahedron Lett. 1998, 39, 8829.
8. (f) Studer, A.; Bossart, M.; Vasella, T. Org. Lett. 2000, 2, 985.
9. (a) da Mata, M. L. E. N.; Motherwell, W. B.; Ujjainwalla, F. Tetrahedron Lett. 1997, 38, 137.
10. (b) da Mata, M. L. E. N.; Motherwell, W. B.; Ujjainwalla, F. Tetrahedron Lett. 1997, 38, 141.
11. (c) Speckamp, W. N.; Köhler, J. J. Chem. Soc., Chem. Commun. 1978, 166.
12. (d) Speckamp, W. N.; Loven, R. Tetrahedron Lett. 1972, 16, 1567.
13. (e) Studer, A.; Bossart, M. Chem. Commun. 1998, 2127.
14. Benati, L.; Spagnolo, P.; Tundo, A.; Zanardi, G. J. Chem. Soc., Chem. Commun. 1979, 141.
15. (a) Rosa, A. M.; Lobo, A. M.; Branco, P. S.; Prabhakar, S. Tetrahedron Lett. 1997, 53, 285.
16. (b) Leardini, R.; McNab, H.; Nanni, D. Tetrahedron 1995, 51, 12143.
17. (c) Lee, E.; Lee, C.; Tae, J. S.; Whang, H. S.; Li, K. S. Tetrahedron Lett. 1993, 34, 2343.
18. Clive, D. L. J.; Kang, S. Tetrahedron Lett. 2000, 41, 1315.
19. (a) Yorimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1998, 63, 8604.
20. (b) Nakamura, T.; Yorimitsu, H.; Shinokubo, H.; Oshima, K. Synlett 1998, 1351.
21. (a) Curran, D. P.; Chen, M.-H.; Kim, D. J. Am. Chem. Soc. 1986, 108, 2489.
22. (b) Curran, D. P. Synthesis 1988, 417, 489.
23. Under higher dilution conditions (50 mL of benzene per mmol of 1a), the yield of 3a decreased to 67%.
24. Various solvents were also examined. Notably, the use of anisole instead of benzene resulted in shortening the reaction time, and the reaction went to completion within 1 h at 120°C.
25. 4, and concentrated. Purification by silica gel column chromatography gave 3b (0.36 g, 0.7 mmol) in 70% yield.
26. One-pot reaction starting from 3-butenyldimethylphenyltin and perfluoroalkyl iodide was unsuccessful. For example, treatment of 3-butenyldimethylphenyltin (1.0 mmol) and perfluorobutyl iodide (1.1 mmol) with triethylborane in refluxing benzene (5 mL) for 6 h afforded the corresponding adduct 3b in only 32% yield. Several factors such as the concentration of the substrate would be concerned with the unsatisfactory yield.
27. The reaction did not proceed when AIBN was used instead of triethylborane. We assume a 2-cyano-2-propyl radical, because of its low reactivity, could not abstract iodine atom in 1.
28. (a) Curran, D. P.; Xu, J.; Lazzarini, E. J. Am. Chem. Soc. 1995, 117, 6603.
29. (b) Curran, D. P.; Xu, J.; Lazzarini, E. J. Chem. Soc., Perkin Trans. 1 1995, 3049.
30. (c) Curran, D. P.; Xu, J. J. Chem. Soc., Perkin Trans. 1 1995, 3061.
31. (d) Martinez-Grau, A.; Curran, D. P. J. Org. Chem. 1995, 60, 8332.
32. (e) Martinez-Grau, A.; Curran, D. P. Tetrahedron 1997, 53, 5679.
33. (f) Curran, D. P.; Xu, J. Synlett 1997, 1102.
34. (g) Studer, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 462.
35. (h) Studer, A.; Steen, H. Chem. Eur. J. 1999, 5, 759.
36. Hanessian, S.; Leger, R. J. Am. Chem. Soc. 1992, 114, 3115.