Synthesis of biaryls by intramolecular radical aryl migration from silicon to carbon

Organic Letters

Volumn 2, Issue 7, 2000, Pages 985-988

  Studer, Armido ^a   Bossart, Martin ^a   Vasella, Tomaso ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001178882     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005661f     Document Type: Article

References (42)

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18. Studer, A.; Bossart, M.; Steen, H. Tetrahedron Lett. 1998, 39, 8829. Amrein, S.; Bossart, M.; Vasella, T.; Studer, A. Submitted for publication. For stereoselective radical aryl migrations from sulfur to C-centered radicals, see: Studer, A.; Bossart, M. Chem. Commun. 1998, 2127.
19. Studer, A.; Bossart, M.; Steen, H. Tetrahedron Lett. 1998, 39, 8829. Amrein, S.; Bossart, M.; Vasella, T.; Studer, A. Submitted for publication. For stereoselective radical aryl migrations from sulfur to C-centered radicals, see: Studer, A.; Bossart, M. Chem. Commun. 1998, 2127.
20. Studer, A.; Bossart, M.; Steen, H. Tetrahedron Lett. 1998, 39, 8829. Amrein, S.; Bossart, M.; Vasella, T.; Studer, A. Submitted for publication. For stereoselective radical aryl migrations from sulfur to C-centered radicals, see: Studer, A.; Bossart, M. Chem. Commun. 1998, 2127.
21. To the best of our knowledge, radical aryl migrations from silicon to aryl radicals are unknown. For early reports on the aryl migration from Si to primary C-centered radicals, see: Wilt, J. W.; Dockus, C. F. J. Am. Chem. Soc. 1970, 92, 5813. Wilt, J. W.; Chwang, W. K. J. Am. Chem. Soc. 1974, 96, 6194. Wilt, J. W.; Chwang, W. K.; Dockus, C. F.; Tomiuk, N. M. J. Am. Chem. Soc. 1978, 100, 5534. Sakurai, H.; Hosomi, A. J. Am. Chem. Soc. 1970, 92, 7507.
22. To the best of our knowledge, radical aryl migrations from silicon to aryl radicals are unknown. For early reports on the aryl migration from Si to primary C-centered radicals, see: Wilt, J. W.; Dockus, C. F. J. Am. Chem. Soc. 1970, 92, 5813. Wilt, J. W.; Chwang, W. K. J. Am. Chem. Soc. 1974, 96, 6194. Wilt, J. W.; Chwang, W. K.; Dockus, C. F.; Tomiuk, N. M. J. Am. Chem. Soc. 1978, 100, 5534. Sakurai, H.; Hosomi, A. J. Am. Chem. Soc. 1970, 92, 7507.
23. To the best of our knowledge, radical aryl migrations from silicon to aryl radicals are unknown. For early reports on the aryl migration from Si to primary C-centered radicals, see: Wilt, J. W.; Dockus, C. F. J. Am. Chem. Soc. 1970, 92, 5813. Wilt, J. W.; Chwang, W. K. J. Am. Chem. Soc. 1974, 96, 6194. Wilt, J. W.; Chwang, W. K.; Dockus, C. F.; Tomiuk, N. M. J. Am. Chem. Soc. 1978, 100, 5534. Sakurai, H.; Hosomi, A. J. Am. Chem. Soc. 1970, 92, 7507.
24. To the best of our knowledge, radical aryl migrations from silicon to aryl radicals are unknown. For early reports on the aryl migration from Si to primary C-centered radicals, see: Wilt, J. W.; Dockus, C. F. J. Am. Chem. Soc. 1970, 92, 5813. Wilt, J. W.; Chwang, W. K. J. Am. Chem. Soc. 1974, 96, 6194. Wilt, J. W.; Chwang, W. K.; Dockus, C. F.; Tomiuk, N. M. J. Am. Chem. Soc. 1978, 100, 5534. Sakurai, H.; Hosomi, A. J. Am. Chem. Soc. 1970, 92, 7507.
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27. For reviews, see: Bols, M.; Skrydstrup, T. Chem. Rev. 1995, 95. 1253. Fensterbank, L.; Malacria, M.; Sieburth, S. McN. Synthesis 1997, 813.
28. 3 in pyridine/toluene (1:1, 64%).
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32. Studer, A.; Steen, H. Chem. Eur. J. 1999, 5, 759.
33. In the desilylation, an excess of MeLi was used in order to transform the tributyltin bromide formed as a byproduct in the aryl migration to methyltributylstannane, which is easily removed by chromatography. See also: Crich, D.; Sun, S. J. Org. Chem. 1996, 61, 7200. Renaud, P.; Lacôte, E.; Quaranta, L. Tetrahedron Lett. 1998, 39, 2123.
34. In the desilylation, an excess of MeLi was used in order to transform the tributyltin bromide formed as a byproduct in the aryl migration to methyltributylstannane, which is easily removed by chromatography. See also: Crich, D.; Sun, S. J. Org. Chem. 1996, 61, 7200. Renaud, P.; Lacôte, E.; Quaranta, L. Tetrahedron Lett. 1998, 39, 2123.
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38. The chlorosilanes were prepared according to known procedures (see ref 16) starting from the corresponding di(aryl)dichlorosilanes, see Supporting Information.
39. Schiesser, C. H.; Wild, L. M. Tetrahedron 1996, 52, 13265.
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