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Volumn 64, Issue 5, 1999, Pages 1684-1688

Cross-coupling reactions of hypervalent siloxane derivatives: An alternative to Stille and Suzuki couplings

Author keywords

[No Author keywords available]

Indexed keywords

SILOXANE;

EID: 0033525838     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982463h     Document Type: Article
Times cited : (190)

References (55)
  • 16
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    • The Chapel River Press Ltd.: Andover, Hants, England
    • Siloxanes have been widely used industrially in the production of fluids, resins, elastomers, rubbers, polymers, and miscellaneous products. Because many siloxane polymers are readily prepared by hydrolysis of functionalized siloxane monomers, the preparation of these monomers is well-developed. For more information, see: (a) Freeman, G. G. Silicones: An Introduction to Their Chemistry and Applications; The Chapel River Press Ltd.: Andover, Hants, England, 1962; pp 1-21 and 105-110.
    • (1962) Silicones: An Introduction to Their Chemistry and Applications , pp. 1-21
    • Freeman, G.G.1
  • 17
    • 0039377366 scopus 로고
    • Kumar Das, V. G., Weng, N. G., Gielen, M., Eds.; Oxford University Press: New York
    • (b) Mehrotra, R. C. In Chemistry and Technology of Silicon and Tin; Kumar Das, V. G., Weng, N. G., Gielen, M., Eds.; Oxford University Press: New York, 1992; pp 93-109. For information regarding toxicology studies of silicone products, see:
    • (1992) Chemistry and Technology of Silicon and Tin , pp. 93-109
    • Mehrotra, R.C.1
  • 18
  • 19
    • 0001831159 scopus 로고    scopus 로고
    • Smith, P. J., Ed.; Blackie Academic & Professional: London
    • (d) Arakawa, Y. In Chemistry of Tin, 2nd ed.; Smith, P. J., Ed.; Blackie Academic & Professional: London, 1998; pp 388-428.
    • (1998) Chemistry of Tin, 2nd Ed. , pp. 388-428
    • Arakawa, Y.1
  • 20
    • 0344438252 scopus 로고    scopus 로고
    • Smith, P. J., Ed.; Blackie Academic & Professional: London
    • (e) Smith, P. J. Ibid. Smith, P. J., Ed.; Blackie Academic & Professional: London, 1998; pp 429-441.
    • (1998) Chemistry of Tin, 2nd Ed. , pp. 429-441
    • Smith, P.J.1
  • 21
    • 0041156645 scopus 로고
    • Kumar Das, V. G., Weng, N. G., Gielen, M., Eds.; Oxford University Press: New York
    • (f) Aldridge, W. N. In Chemistry and Technology of Silicon and Tin; Kumar Das, V. G., Weng, N. G., Gielen, M., Eds.; Oxford University Press: New York, 1992; pp 78-92.
    • (1992) Chemistry and Technology of Silicon and Tin , pp. 78-92
    • Aldridge, W.N.1
  • 22
    • 0000390817 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Germany
    • For recent reviews on organosilicon compounds and cross-coupling reactions, see: (a) Hiyama, T. In Metal-catalyzed Cross-coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinhein, Germany, 1998; pp 421-452.
    • (1998) Metal-catalyzed Cross-coupling Reactions , pp. 421-452
    • Hiyama, T.1
  • 23
    • 0000185390 scopus 로고
    • (b) Horn, K. A. Chem. Rev. 1995, 95, 1317-1350.
    • (1995) Chem. Rev. , vol.95 , pp. 1317-1350
    • Horn, K.A.1
  • 27
    • 0000121752 scopus 로고    scopus 로고
    • For information about Pd-catalyzed, fluoride promoted cross-coupling reactions of reactions of organohalosilanes with aryl and alkenyl-halides see: (a) Gouda, K.; Hagiwara, E.; Hatanaka, Y.; Hiyama, T. J. Org. Chem. 1996, 61, 7232-7233.
    • (1996) J. Org. Chem. , vol.61 , pp. 7232-7233
    • Gouda, K.1    Hagiwara, E.2    Hatanaka, Y.3    Hiyama, T.4
  • 30
    • 0002376946 scopus 로고
    • (d) Hatanaka, Y.; Fukushima, S.; Hiyama, T. Chem. Lett. 1989, 1711-1714. For information about alkylation of aryl halides with alkyltrifluorosilanes, see:
    • (1989) Chem. Lett. , pp. 1711-1714
    • Hatanaka, Y.1    Fukushima, S.2    Hiyama, T.3
  • 36
    • 0001689307 scopus 로고    scopus 로고
    • Brescia, M.-R.; DeShong, P. J. Org. Chem. 1998, 63, 3156-3157. See also ref 7. For other papers relating to the application of hypervalent silicates as reagents, see: (a) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901-6905.
    • (1998) Org. Chem. , vol.63 , pp. 3156-3157
    • Brescia, M.-R.1    DeShong, P.J.2
  • 37
    • 0001443339 scopus 로고    scopus 로고
    • Brescia, M.-R.; DeShong, P. J. Org. Chem. 1998, 63, 3156-3157. See also ref 7. For other papers relating to the application of hypervalent silicates as reagents, see: (a) Pilcher, A. S.; DeShong, P. J. Org. Chem. 1996, 61, 6901-6905.
    • (1996) J. Org. Chem. , vol.61 , pp. 6901-6905
    • Pilcher, A.S.1    DeShong, P.2
  • 42
    • 0344870045 scopus 로고    scopus 로고
    • note
    • The mechanism of this remarkable fluoride-induced homocoupling of aryl iodides by Pd is under investigation.
  • 43
    • 0001496228 scopus 로고    scopus 로고
    • The presumed mechanism for these types of cross-coupling reactions is as follows: formation of the hypervalent organosilane, oxidative addition of Pd(0) to the aryl or alkyl halide, followed by transmetalation of the hypervalent organosilane to the organopalladium(II) complex. Reductive elimination then occurs, giving the cross-coupled adduct, Pd(0), and a tetravalent organosilane. The transmetalation adduct using Hiyama-type conditions was recently isolated. For more information, see: Mateo, C.; Fernandez-Rivas, C.; Echavarren, A. M.; Cardenas, D. J. Organometallics 1997, 16, 1997-1999.
    • (1997) Organometallics , vol.16 , pp. 1997-1999
    • Mateo, C.1    Fernandez-Rivas, C.2    Echavarren, A.M.3    Cardenas, D.J.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.