New access to cross-coupling reaction between arylsilanes or heteroarylsilanes and aryl halides mediated by a copper(I) salt

Chemistry Letters

Volumn , Issue 7, 1997, Pages 639-640

  Ito, Hajime ^a   Sensui, Hiro Omi ^a   Arimoto, Kikuo ^a   Miura, Katsukiyo ^a   Hosomi, Akira ^a  

^a UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031525248     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1997.639     Document Type: Article

References (15)

1. Studies on Organosilicon Chemistry. No. 135.
2. For recent reports, see: K. Goda, E. Ejiri, Y. Hatanaka, and T. Hiyama, J. Org. Chem., 61, 7232 (1996); T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 66, 1471 (1994); K. Tamao, K. Kobayashi, and Y. Ito, Tetrahedron Lett., 30, 6051 (1989).
3. For recent reports, see: K. Goda, E. Ejiri, Y. Hatanaka, and T. Hiyama, J. Org. Chem., 61, 7232 (1996); T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 66, 1471 (1994); K. Tamao, K. Kobayashi, and Y. Ito, Tetrahedron Lett., 30, 6051 (1989).
4. For recent reports, see: K. Goda, E. Ejiri, Y. Hatanaka, and T. Hiyama, J. Org. Chem., 61, 7232 (1996); T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 66, 1471 (1994); K. Tamao, K. Kobayashi, and Y. Ito, Tetrahedron Lett., 30, 6051 (1989).
5. A. Hosomi, Heteroatom Chemistry, 7, 214 (1992);
6. M. Hojo, C. Murakami, H. Aihara, E. Komori, S. Kohra, Y. Tominaga, and A. Hosomi, Bull. Soc. Chim. Fr., 132, 499 (1995).
7. The fluoride ion-free cross-coupling reaction between alkenylfluorosilanes and allylic carbonates catalyzed by a Pd complex was reported, see: H. Matsuhashi, Y. Hatanaka, M. Kuroboshi, and T. Hiyama, Tetrahedron Lett., 36, 1539 (1995).
8. Trifluoromethylation of organic halides using trifluoromethyltriethylsilane, KF and Cu(I) was reported, see: H. Urata and T. Fuchikami, Tetrahedron Lett., 32, 91 (1991). In this reaction the fluoride ion was essential for the promotion of the reaction.
9. The solid-state homo-coupling reaction of alkenylpentafluorosilicates promoted by CuCl was reported, see: J. Yoshida, K. Tamao, T. Kakui, and M. Kumada, Tetrahedron Lett., 1979, 1141.
10. A. Dondoni, G. Fantin, M. Fogagnolo, A. Medici, and P. Pedrini, J. Org. Chem., 53, 1748 (1988).
11. This trend can be reasonably explained by the formation energies of Si-X bonds produced by this group transfer reaction from silicon to copper.
12. Other copper(I) alkoxides and aryloxides such as methoxide, t-butoxide, and phenoxide show stronger affinity to the organic halides than the organosilicon compounds. In particular, an addition of sodium phenoxide or 4-methoxyphenoxide selectively produced diphenyl ether derivatives (e.g., eq. 5). equation presented
13. Sodium pentafluorophenoxide was prepared from sodium hydride (2.26 g, 94 mmol) and pentafluorophenol (11.3 g, 61.4 mmol) in dry THF (50 mL). After filtration and evaporation in vacuo, the residue (12.6 g, 61.2 mmol) was dissolved in dry DMI (15.3 mL).
14. 3) δ -1.7, 36.5, 50.3, 107.9, 120.6, 127.3, 130.0. See, S. Gronowitz and R. Kada, J. Heterocyclic Chem., 21, 1041 (1984).
15. 3) δ 1.29, 50.7, 128.2, 131.2, 135.1, 136.7.