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Volumn 132, Issue 34, 2010, Pages 11838-11840

Synthesis of 3-trifluoromethylbenzo[ b ]furans from phenols via direct ortho functionalization by extended pummerer reaction

Author keywords

[No Author keywords available]

Indexed keywords

ANNULATION REACTIONS; FUNCTIONALIZATIONS; METHYLTHIO GROUP;

EID: 77956067595     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja1030134     Document Type: Article
Times cited : (141)

References (43)
  • 12
    • 77956079064 scopus 로고    scopus 로고
    • Our additional reports
    • Our additional reports
  • 15
    • 77956088330 scopus 로고    scopus 로고
    • Reviews about conventional extended Pummerer reactions
    • Reviews about conventional extended Pummerer reactions
  • 26
    • 77956078452 scopus 로고    scopus 로고
    • A 4/1 mixture of E / Z isomers was used. We confirmed that the reactivities of the two isomers are approximately identical
    • A 4/1 mixture of E / Z isomers was used. We confirmed that the reactivities of the two isomers are approximately identical.
  • 28
    • 77956089372 scopus 로고    scopus 로고
    • Palladium-catalyzed annulation with trifluoromethylalkynes
    • Palladium-catalyzed annulation with trifluoromethylalkynes
  • 31
    • 77956067350 scopus 로고    scopus 로고
    • Copper-mediated trifluoromethylation with trifluoroiodomethane
    • Copper-mediated trifluoromethylation with trifluoroiodomethane
  • 34
    • 77956093142 scopus 로고    scopus 로고
    • -. Although a methyl or phenyl group could not replace the trifluoromethyl group of 1b, substitution of the trifluoromethyl group with a heptadecafluorooctyl group successfully led to the formation of 2-methylthio-3-heptadecafluorooctylbenzo[ b ]furan (5a′) in 85% yield
    • -. Although a methyl or phenyl group could not replace the trifluoromethyl group of 1b, substitution of the trifluoromethyl group with a heptadecafluorooctyl group successfully led to the formation of 2-methylthio-3-heptadecafluorooctylbenzo[ b ]furan (5a′) in 85% yield.
  • 35
    • 77956082953 scopus 로고    scopus 로고
    • The methylthio group of 1b would be important to precisely control the reactivity of the cationic intermediate 7. Replacing the methylthio group of 1b with a phenyl or methoxyphenyl group, which can stabilize cationic intermediates, failed to afford the corresponding 2-arylbenzofurans
    • The methylthio group of 1b would be important to precisely control the reactivity of the cationic intermediate 7. Replacing the methylthio group of 1b with a phenyl or methoxyphenyl group, which can stabilize cationic intermediates, failed to afford the corresponding 2-arylbenzofurans.
  • 36
    • 77956075062 scopus 로고    scopus 로고
    • The structure was determined by X-ray crystallographic analysis as well as NMR spectroscopy
    • The structure was determined by X-ray crystallographic analysis as well as NMR spectroscopy.
  • 37
    • 77956089839 scopus 로고    scopus 로고
    • Pd-catalyzed cross-coupling of reactive N -heteroaryl sulfides with organozinc reagent was reported
    • Pd-catalyzed cross-coupling of reactive N -heteroaryl sulfides with organozinc reagent was reported


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.