Synthesis of allylsilanes and dienylsilanes by a one-pot catalytic C-H borylation-Suzuki-Miyaura coupling sequence

Organic Letters

Volumn 10, Issue 14, 2008, Pages 3129-3131

  Olsson, Vilhelm J ^a   Szabó, Kálmán J ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALLYLSILANE; BORONIC ACID DERIVATIVE; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALKENES; BORONIC ACIDS; CATALYSIS; MOLECULAR STRUCTURE; SILANES; STEREOISOMERISM;

EID: 52049114730     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801203u     Document Type: Article

References (39)

1. (a) Fleming, I.; Barbero, A.; Walter, D Chem. Rev 1997, 97, 2063.
2. (b) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry; Wiley: Chichester, 2002.
3. (c) Sarkar, T. K. Science of Synthesis, Houben-Weyl Methods of Molecular Transformations; Fleming, I., Ed.; Thieme: Stuttgart, 2002; Vol. 4, p 837.
4. (d) Langkopf, E.; Schinzer, D. Chem. Rev. 1995, 95, 1375.
5. (e) Chabaud, L.; James, P.; Landais, Y. Eur. J. Org. Chem. 2004, 3173.
6. (f) Chan, T. H. Chem. Rev. 1995, 95, 1279.
7. (g) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
8. (h) Kacprzynski, M. A.; May, T. L.; Kazane, S. A.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 4554.
9. (i) Nakamura, S.; Uchiyama, M.; Ohwada, T. J. Am. Chem. Soc. 2005, 127, 13116.
10. (j) Huber, J. D.; Perl, N. R.; Leighton, J. L. Angew. Chem., Int. Ed. 2008, 47, 3037.
11. (k) Auer, G.; Oestreich, M. Adv. Synth. Catal. 2005, 347, 637.
12. (l) Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem. 1985, 50, 3896.
13. (m) Macsári, I.; Hupe, E.; Szabó, K. J. J. Org. Chem. 1999, 64, 9547.
14. (n) Macsári, I.; Szabó, K. J. Chem. Eur. J. 2001, 7, 4097.
15. (o) Barbero, A.; Cuadrado, P.; Fleming, I.; González, A. M.; Pulido, F. J. J. Chem. Soc., Perkin Trans. 1 1992, 327.
16. (p) Hayashi, T.; Konishi, M.; Ito, H.; Kumada, M. J. Am. Chem. Soc. 1982, 104, 4962.
17. (a) Mkhalid, I. A. I.; Coventry, D. N.; Albesa-Jove, D.; Batsanov, A. S.; Howard, J. A. K.; Perutz, R. N.; Marder, T. B. Angew. Chem., Int. Ed. 2006, 45, 489.
18. (b) Coapes, R. B.; Souza, F. E. Z.; Thomas, R. L.; Hall, J. J.; Marder, T. B. Chem. Commun. 2003, 614.
19. (c) Mkhalid, I. A. I; Coapes, B.; Edes, N.; Coventry, D. N.; Souza, F. E. S.; Thomas, R. L.; Hall, J. J.; Bi, S.-W.; Lin, Z.; Marder, T. B. Dalton Trans. 2008, 1055.
20. (d) Burgess, K.; van der Donk, W. A.; Westcott, S. A.; Marder, T. B.; Baker, R. T.; Calabrese, J. C. J. Am. Chem. Soc. 1992, 114, 9350.
21. (e) Tzschucke, C. C.; Murphy, J. M.; Hartwig, J. F. Org. Lett. 2007, 9, 761.
22. (f) Boller, T. M.; Murphy, J. M.; Hapke, M.; Ishiyama, T.; Miyaura, N.; Hartwig, J. F. J. Am. Chem. Soc. 2005, 127, 14263.
23. (g) Cho, J. Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E.; Smith, M. R. Science 2002, 295, 305.
24. (h) Olsson, V. J.; Szabo, K. J. Angew. Chem., Int. Ed. 2007, 46, 6891.
25. (i) Brown, J. M.; Lloyd-Jones, G. C. J. Am. Chem. Soc. 1994, 116, 866.
26. (a) Hall, D. G. Boronic Acids; Wiley: Weinheim, 2005.
27. (b) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
28. (c) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
29. Kjellgren, J.; Aydin, J.; Saltanova, I. V.; Wallner, O. A.; Szabo, K. Chem. Eur. J. 2005, 11, 5260.
30. (a) Lee, T. W.; Corey, E. J J. Am. Chem. Soc. 2001, 123, 1872.
31. (b) Meyers, C. Y.; Hua, D. H.; Peacock, N. J. J. Org. Chem. 1980, 45, 1721.
32. (c) Yasuda, H.; Nishi, T.; Miyanaga, S.; Nakamura, A. Organometallics 1985, 4, 359.
33. (a) Li, D.; Liu, G.; Hu, Q.; Wang, C.; Xi, Z. Org. Lett. 2007, 9, 5433.
34. (b) Urabe, H.; Mitsui, K.; Ohata, S.; Sato, F. J. Am. Chem. Soc. 2003, 125, 6074.
35. (c) Koreeda, M.; Ciufolini, M. A. J. Am. Chem. Soc. 1982, 104, 2308.
36. (d) Luh, T.-Y.; Wong, K.-T. Synthesis 1993, 349.
37. (a) Pereira, S.; Srebnik, M. Organometallics 1995, 14, 3127.
38. (b) Morrill, C.; Grubbs, R. H. J. Org. Chem. 2003, 68, 6031.
39. (c) Jankowska, M.; Pietraszuk, C.; Marciniec, B.; Zaidlewicz, M. Synlett 2006, 1695.