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Volumn 52, Issue 21, 2011, Pages 2638-2641

Asymmetric Suzuki-Miyaura cross-coupling of aryl chlorides with enhancement of reaction time and catalyst turnover

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; CHLORIDE; ORGANOPHOSPHORUS COMPOUND; PALLADIUM;

EID: 79955478783     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.03.051     Document Type: Article
Times cited : (26)

References (65)
  • 1
    • 57549099215 scopus 로고    scopus 로고
    • For reviews on Suzuki-Miyaura cross-coupling reaction, see: R. Martin, and S.L. Buchwald Acc. Chem. Res. 41 2008 1461 1473
    • (2008) Acc. Chem. Res. , vol.41 , pp. 1461-1473
    • Martin, R.1    Buchwald, S.L.2
  • 48
    • 79955479252 scopus 로고    scopus 로고
    • The phosphonite 2, 3, and 4 were applied in the formation of tetra-ortho-substituted biaryl: a cross-coupling reaction with 2-(2-chloro-3-methoxyphenyl)-1,3-dioxolane of 2,4,6-trimethylphenylboronic acid. However, any coupling adduct was not observed
    • The phosphonite 2, 3, and 4 were applied in the formation of tetra-ortho-substituted biaryl: a cross-coupling reaction with 2-(2-chloro-3-methoxyphenyl)-1,3-dioxolane of 2,4,6-trimethylphenylboronic acid. However, any coupling adduct was not observed.
  • 49
    • 79955477868 scopus 로고    scopus 로고
    • note
    • 2P: C, 88.38; H, 5.44. Found: C, 88.28; H, 5.46.
  • 61
    • 79955471221 scopus 로고    scopus 로고
    • note
    • 3: C, 75.53; H, 6.71. Found: C, 75.52; H, 6.75.
  • 63
    • 79955465237 scopus 로고    scopus 로고
    • 1H NMR data of a biaryl bearing axial chirality (R)
    • 1H NMR data of a biaryl bearing axial chirality (R).
  • 64
    • 79955463013 scopus 로고    scopus 로고
    • The biaryl product in entries 10 and 11 was purified by recrystallization one time to remove small amounts of unclear byproducts
    • The biaryl product in entries 10 and 11 was purified by recrystallization one time to remove small amounts of unclear byproducts.
  • 65
    • 79955483858 scopus 로고    scopus 로고
    • Unfortunately, the derivatives from the cross-coupling reactions of 2-chrolo-3-methoxy benzonitrile 9 with ortho-tolylboronic acid 8, ortho-methoxyphenlylboronic acid 10, and ortho-formylphenylboronic acid did not have enough rotation barriers to maintain the axial chirality. The spectra of HPLC indicate that these bialys are racemic compounds even at 298 K
    • Unfortunately, the derivatives from the cross-coupling reactions of 2-chrolo-3-methoxy benzonitrile 9 with ortho-tolylboronic acid 8, ortho-methoxyphenlylboronic acid 10, and ortho-formylphenylboronic acid did not have enough rotation barriers to maintain the axial chirality. The spectra of HPLC indicate that these bialys are racemic compounds even at 298 K.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.