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Volumn 4, Issue 21, 2002, Pages 3771-3774

Cross-coupling reactions of alkenylsilanols with fluoroalkylsulfonates

Author keywords

[No Author keywords available]

Indexed keywords

SILANE DERIVATIVE; SILANOL; SULFONIC ACID DERIVATIVE;

EID: 0037126205     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026900x     Document Type: Article
Times cited : (67)

References (37)
  • 3
    • 0042770831 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, Chapter 4
    • (c) Mitchell, T. N. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Chapter 4.
    • (1998) Metal-catalyzed Cross-coupling Reactions
    • Mitchell, T.N.1
  • 5
    • 0042770830 scopus 로고    scopus 로고
    • Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, Chapter 2
    • (b) Suzuki, A. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim, Germany, 1998; Chapter 2.
    • (1998) Metal-catalyzed Cross-coupling Reactions
    • Suzuki, A.1
  • 13
    • 84943904705 scopus 로고
    • Other nonhalide coupling partners for palladium-catalyzed cross-couplings include iodonium salts: (a) Hinkle, R. J.; Poulter, G. T.; Stang, P. J. J. Am. Chem. Soc. 1993, 115, 11626.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 11626
    • Hinkle, R.J.1    Poulter, G.T.2    Stang, P.J.3
  • 27
    • 0025283733 scopus 로고
    • Hiyama has reported the cross-coupling of fluorosilanes to aryl and alkenyl inflates. Hatanaka, Y.; Hiyama, T. Tetrahedron Lett. 1990, 31, 2719.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 2719
    • Hatanaka, Y.1    Hiyama, T.2
  • 28
    • 0033214303 scopus 로고    scopus 로고
    • It has been reported that nonaflates are less susceptible than inflates to nucleophilic attack at the sulfur atom, which we believe to be the source of undesired phenol formation. See: Neuville, L.; Bigot, A.; Dau, M. E. T. H.; Zhu, J. J. Org. Chem. 1999, 64, 7638.
    • (1999) J. Org. Chem. , vol.64 , pp. 7638
    • Neuville, L.1    Bigot, A.2    Dau, M.E.T.H.3    Zhu, J.4
  • 29
    • 0043272119 scopus 로고    scopus 로고
    • note
    • 3, CsOH, and NaOMe.
  • 32
    • 0035925228 scopus 로고    scopus 로고
    • For a review on water-accelerated organic transformations, see: Ribe, S.; Wipf, P. Chem. Commun. 2001, 299.
    • (2001) Chem. Commun. , pp. 299
    • Ribe, S.1    Wipf, P.2
  • 33
    • 0000477767 scopus 로고
    • Reduced nucleophilicity of tetrahexylammonium fluoride with increasing levels of hydration has been reported: Landini, D.; Maia, A.; Rampoldi, A. J. Org. Chem. 1989, 54, 328.
    • (1989) J. Org. Chem. , vol.54 , pp. 328
    • Landini, D.1    Maia, A.2    Rampoldi, A.3
  • 34
    • 0034366130 scopus 로고    scopus 로고
    • It has been suggested that a stable geometry exists as six water molecules around the fluoride ion of TBAF in an aqueous solution. See: Craig, J. D. C.; Booker, M. H. J. Solution Chem. 2000, 29, 879.
    • (2000) J. Solution Chem. , vol.29 , pp. 879
    • Craig, J.D.C.1    Booker, M.H.2
  • 36
    • 0042269618 scopus 로고    scopus 로고
    • note
    • Lower yields of these couplings result from problematic separation of the hydrocarbon product from the polymethylsiloxane byproducts.
  • 37
    • 0042269617 scopus 로고    scopus 로고
    • note
    • 3e


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.