Catalytic activation of silylated nucleophiles using tBu-P4 as a base

European Journal of Organic Chemistry

Volumn , Issue 10, 2005, Pages 1965-1968

  Ueno, Masahiro ^a   Hori, Chieko ^a   Suzawa, Koichi ^a   Ebisawa, Masashi ^a   Kondo, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Anions; Aromatic compounds; Catalysis; Phosphazenes

Indexed keywords

EID: 19844367398     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500087     Document Type: Article

References (36)

1. a) M. A. Brook, Silicon in Organic, Organometallic, and Polymer Chemistry, John Wiley & Sons, New York, 2000;
2. b) E. Colvin, Silicon in Organic Synthesis, Butterworth, London, 1981;
3. c) W. P. Weber, Silicon Reagents for Organic Synthesis, Springer-Verlag, Berlin, 1983.
4. T. W. Green, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., Wiley, New York, 1999.
5. a) T. Imahori, Y. Kondo, J. Am. Chem. Soc. 2003, 125, 8082-8083;
6. b) M. Uchiyama, T. Miyoshi, Y. Kajihara, T. Sakamoto, Y. Otani, T. Ohwada, Y. Kondo, J. Am. Chem. Soc. 2002, 124, 8514-8515;
7. c) Y. Kondo, M. Shilai, M. Uchiyama, T. Sakamoto, J. Am. Chem. Soc. 1999, 121, 3539-3540.
8. T. Imahori, C. Hori, Y. Kondo, Adv. Synth. Catal. 2004, 346, 1090-1092.
9. a) R. Schwesinger, H. Schlemper, Angew. Chem. Int. Ed. Engl. 1987, 26, 1167-1169;
10. b) R. Schwesinger, H. Schlemper, C. Hasenfratz, J. Willaredt, T. Dambacher, T. Breuer, C. Ottaway, M. Fletschinger, J. Boele, H. Fritz, D. Putzas, H. W. Rotter, F. G. Bordwell, A. V. Satish, G.-Z. Ji, E.-M. Peters, K. Peters, H. G. von Schnering, L. Walz, Liebigs Ann. 1996, 1055-1081.
11. a) G. A. Kraus, N. Zhang, J. G. Verkade, M. Nagarajan, P. B. Kisanga, Org. Lett. 2000, 2, 2409-2410;
12. b) T. Pietzonka, D. Seebach, them. Ber. 1991, 124, 1837-1843;
13. c) T. Pietzonka, D. Seebach, Angew. Chem. Int. Ed. Engl. 1993, 32, 716-717;
14. d) I. Leito, T. Rodima, I. A. Koppel, R. Schwesinger, V. M. Vlasov, J. Org. Chem. 1997, 62, 8479-8483;
15. e) H. Schlaad, H. Kukula, J. Rudloff, I. Below, Macromolecules 2001, 34, 4302-4304.
16. For nucleophilic cleavage of a nucleophile-silicon bond, see: a) T. D. Nelson, R. D. Crouch, Synthesis 1996, 1031-1069;
17. b) J. G. Verkade, P. B. Kisanga, Tetrahedron 2003, 59, 7819-7858 and references cited therein. See also ref. [1].
18. For recent biaryl ether synthesis using heavy metal catalysts see: Pd: a) G. Mann, Q. Shelby, A. H. Roy, J. F. Hartwig, Organometallics 2003, 22, 2775-2789;
19. b) N. Kataoka, Q. Shelby, J. P. Stambuli, J. F. Hartwig, J. Org. Chem. 2002, 67, 5553-5566;
20. Q. Shelby, N. Kataoka, G. Mann, J. Hartwig, J. Am. Chem. Soc. 2000, 122, 10 718-10 719;
21. Cu: d) D. Ma, Q. Cai, Org. Lett. 2003, 5, 3799-3802;
22. e) E. Buck, Z. J. Song, D. Tschaen, P. G. Dormer, R. P. Volante, P. J. Reider, Org. Lett. 2002, 4, 1623-1626;
23. f) R. K. Gujadhur, C. G. Bates, D. Venkataraman, Org. Lett. 2001, 3, 4315-4317.
24. As a suggested example of the use of stoichiometric tBu-P4 base for promoting the Ullman reaction see: C. Palomo, M. Oiarbide, R. López, E. Gómez-Bengoa, Chem. Commun. 1998, 2091-2092.
25. N. E. Leadbeater, M. Marco, B. J. Tominack, Org. Lett. 2003, 5, 3919-3922.
26. For the 1,2-carbonyl addition of 2-TMS-benzothiazole see: F. Effenberger, W. Spiegier, Chem. Ber. 1985, 118, 3872-3899.
27. A. S. Pilcher, P. DeShong, J. Org. Chem. 1996, 61, 6901-6905.
28. For base-promoted activation of allylsilanes see: a) Z. Wang, P. Kisanga, J. G. Verkade, J. Org. Chem. 1999, 64, 6459-6461;
29. b) N. Asao, A. Shibato, Y Itagaki, F. Jourdan, K. Maruoka, Tetrahedron Lett. 1998, 39, 3177-3180;
30. c) A. Hosomi, A. Shirahata, H. Sakurai, Tetrahedron Lett. 1978, 19, 3043-3046.
31. For activation of alkynylsilanes see: a) E. Nakamura, E. Kuwajima, Angew. Chem. Int. Ed. Engl. 1976, 15, 498-499;
32. b) I. Kuwajima, E. Nakamura, K. Hashimoto, Tetrahedron 1983, 39, 975-982.
33. For base-promoted hydrosilylation of carbonyl see: a) Y. Kawanami, H. Yuasa, F. Toriyama, S. Yoshida, T. Baba, Catal. Commun. 2003, 4, 455-459;
34. b) Z. Wang, A. E. Wroblewski, J. G. Verkade, J. Org. Chem. 1999, 64, 8021-8023;
35. c) Y. Izumi, H. Nanami, K. Higuchi, M. Onaka, Tetrahedron Lett. 1991, 32, 4741-4744.
36. In order to remove any traces of water, tBu-P4 base was treated with ethyl bromide (ref. [5b]). The "dried P4 base" also showed catalytic reactivity for the activation of alkynylsilanes. However, further careful spectroscopic experiments are necessary to clarify the exact mode of activation; NMR studies are currently underway.