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Volumn 68, Issue 23, 2003, Pages 9151-9154

Cross-Coupling of Alkynylsilanols with Aryl Halides Promoted by Potassium Trimethylsilanolate

Author keywords

[No Author keywords available]

Indexed keywords

COUPLING PROMOTERS;

EID: 0242408512     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0351771     Document Type: Article
Times cited : (50)

References (39)
  • 1
    • 0003799267 scopus 로고
    • Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim
    • For a review of the field, see: Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; Wiley-VCH: Weinheim, 1995.
    • (1995) Modern Acetylene Chemistry
  • 9
    • 0037943974 scopus 로고    scopus 로고
    • For a recent review of organometallic reagents in the Sonogashira reaction, see: Negishi, E.; Anastasia, L. Chem. Rev. 2003, 103, 1979.
    • (2003) Chem. Rev. , vol.103 , pp. 1979
    • Negishi, E.1    Anastasia, L.2
  • 28
    • 0242451825 scopus 로고    scopus 로고
    • note
    • (a) Tetrabutylammonium fluoride (TBAF): (Fluka) $624/mol.
  • 29
    • 0242620311 scopus 로고    scopus 로고
    • note
    • (b) Potassium trimethylsilanolate (KOTMS): (Aldrich) $63/mol.
  • 35
    • 0030990486 scopus 로고    scopus 로고
    • The direct transmetalation of alkynylsilanes to form copper(I) acetylides without an external activator has been previously demonstrated. Ito, H.; Arimoto, K.; Sensui, H.; Hosomi, A. Tetrahedron Lett. 1997, 38, 3977.
    • (1997) Tetrahedron Lett. , vol.38 , pp. 3977
    • Ito, H.1    Arimoto, K.2    Sensui, H.3    Hosomi, A.4
  • 36
    • 0037534218 scopus 로고    scopus 로고
    • We have recently speculated on the possibility of silicon to copper transmetalation in the cross-coupling of electron-deficient alkenes. Denmark, S. E.; Kobayashi, T. J. Org. Chem. 2003, 68, 5153.
    • (2003) J. Org. Chem. , vol.68 , pp. 5153
    • Denmark, S.E.1    Kobayashi, T.2
  • 37
    • 0242535509 scopus 로고    scopus 로고
    • note
    • It should be noted that the TBAF-promoted couplings of alkynylsilanols (ref 8) and terminal alkynes (ref 12a) were performed at 60°C.
  • 38
    • 0242535510 scopus 로고    scopus 로고
    • note
    • 3As.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.