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Volumn 343, Issue 6173, 2014, Pages 853-857

Rhodium-catalyzed intermolecular C-H silylation of arenes with high steric regiocontrol

Author keywords

[No Author keywords available]

Indexed keywords

HYDROGEN; POLYCYCLIC AROMATIC HYDROCARBON; RHODIUM; SILANE;

EID: 84894283977     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1248042     Document Type: Article
Times cited : (287)

References (44)
  • 29
    • 84894263037 scopus 로고    scopus 로고
    • note
    • 2 is commercially available.
  • 30
    • 84894245835 scopus 로고    scopus 로고
    • note
    • For applications of phosphine-ligated rhodium catalysts in intramolecular silylation reactions, see (23, 24).
  • 31
    • 84894244315 scopus 로고    scopus 로고
    • note
    • 3], from hydrosilylation of the hydrogen acceptor, cyclohexene, is the only major side product.
  • 32
    • 84894257579 scopus 로고    scopus 로고
    • note
    • The side reaction, cyclohexene hydrosilylation, consumes both the silane and cyclohexene.
  • 33
    • 84894257127 scopus 로고    scopus 로고
    • note
    • For reactions with 8a, 9a, and 10a, the selectivities of silylation meta and ortho to the methoxy groups are 95.4:4.6, 97.0:3.0, and 97.4:2.6, respectively, as determined by GC analysis. The selectivities for all other 1,3-disubstituted arenes are >99:1.
  • 35
    • 84894269587 scopus 로고    scopus 로고
    • note
    • For silylations of 16a and 17a, the selectivities for reactions at the 2-positions over all other positions are 98:2 and 97:3, respectively.
  • 36
    • 84868156095 scopus 로고    scopus 로고
    • H. Tajuddin et al., Chem. Sci. 3, 3505-3515 (2012).
    • (2012) Chem. Sci. , vol.3 , pp. 3505-3515
    • Tajuddin, H.1
  • 39
    • 84894283372 scopus 로고    scopus 로고
    • note
    • Borylation of benzodioxole following the procedure in (44) afforded a mixture of meta, ortho, and diborylation products (92% yield) in a ratio of 6:33:61. This difference from (38) is likely due to the difference in the amount of the diboron reagent used.
  • 40
    • 84894226398 scopus 로고    scopus 로고
    • note
    • Two constitutional isomers of the borylation product, along with a diborylation product, were obtained in a ratio of 43:18:39 following the literature procedure (44).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.