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Volumn , Issue 5, 2006, Pages 771-775

Rh(I)-catalyzed O-silylation of alcohol with vinylsilane

Author keywords

Alcohol; O H bond cleavage; Silyl ether; Vinylsilane; Wilkinson's complex

Indexed keywords

ALCOHOL; RHODIUM DERIVATIVE; SILANE DERIVATIVE;

EID: 33645392240     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.2106/JBJS.E.00762     Document Type: Article
Times cited : (22)

References (43)
  • 30
    • 33645384642 scopus 로고    scopus 로고
    • note
    • 2Si: C, 66.60; H, 10.11.ound: C, 66.20; H, 10.17.
  • 31
    • 33645400590 scopus 로고    scopus 로고
    • note
    • Only the hydroacylated product 5a was obtained and gave 70% isolated yield when the reaction of 4-hydroxybenzaldehyde (1a) and triethylvinylsilane (2a) was carried out at 130 °C for 5 h under the same catalytic system.
  • 32
    • 33645392475 scopus 로고    scopus 로고
    • note
    • 3RhCl(3), a quantitative yield of benzaldehyde was determined by GCMS. This result implies that the iridium catalyst favors β-hydrogen elimination over β-silyl elimination on the contrary to the rhodium catalyst.
  • 40
    • 3743092578 scopus 로고
    • and references cited therein
    • For a review, see: Bryndza, H. E.; Tam, W. Chem. Rev. 1988, 88, 1163; and references cited therein.
    • (1988) Chem. Rev. , vol.88 , pp. 1163
    • Bryndza, H.E.1    Tam, W.2
  • 41
    • 33645398315 scopus 로고    scopus 로고
    • note
    • 2, n-hexane-EtOAc = 15:1) to afford 41.8 mg (93%) of benzyloxytrimethylsilane (6a).
  • 42
    • 33645380115 scopus 로고    scopus 로고
    • note
    • 2. For a GC analysis, the crude mixture was filtered through a small plug of silica gel to remove the catalyst. The conversion yield, as determined by a GC analysis, was 100%.
  • 43
    • 3042673565 scopus 로고    scopus 로고
    • For a review on selective deprotection of silyl ether, see: Crouch, R. D. Tetrahedron 2004, 60, 5833.
    • (2004) Tetrahedron , vol.60 , pp. 5833
    • Crouch, R.D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.