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Volumn 133, Issue 7, 2011, Pages 2160-2162

Copper-mediated intermolecular direct biaryl coupling

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; C-H BOND CLEAVAGE; COPPER SALT; HIGH POTENTIAL; NEW APPROACHES; PALLADIUM CATALYST; REACTION SYSTEM;

EID: 79951816256     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja111401h     Document Type: Article
Times cited : (215)

References (56)
  • 26
    • 60749131408 scopus 로고    scopus 로고
    • Copper-mediated dehydrogenative intermolecular arylations: (a)
    • Copper-mediated dehydrogenative intermolecular arylations: (a) Jia, Y.-X.; Kündig, E. P. Angew. Chem., Int. Ed. 2009, 48, 1636.
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 1636
    • Jia, Y.-X.1    Kündig, E.P.2
  • 28
    • 33744786786 scopus 로고    scopus 로고
    • Copper-mediated C-H functionalization of 2-phenylpyridines: (a)
    • Copper-mediated C-H functionalization of 2-phenylpyridines: (a) Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 6790
    • Chen, X.1    Hao, X.-S.2    Goodhue, C.E.3    Yu, J.-Q.4
  • 34
    • 35348998959 scopus 로고    scopus 로고
    • Copper-mediated direct arylation of azoles with aryl halides: (a)
    • Copper-mediated direct arylation of azoles with aryl halides: (a) Do, H.-G.; Daugulis, O. J. Am. Chem. Soc. 2007, 129, 12404.
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 12404
    • Do, H.-G.1    Daugulis, O.2
  • 39
    • 79951822111 scopus 로고    scopus 로고
    • note
    • A small amount (ca. 0.060 mmol) of the product of homo-coupling of 2a was observed by GC and GC-MS analyses. The byproduct was readily separated by silica gel column purification. See the Supporting Information for the detailed optimization studies.
  • 40
    • 79951845779 scopus 로고    scopus 로고
    • note
    • 8 remained unsuccessful.
  • 41
    • 79951838826 scopus 로고    scopus 로고
    • note
    • 2 decreased the yield of 3aa by ca. 10%.
  • 42
    • 79951845778 scopus 로고    scopus 로고
    • note
    • The reactions of 1a with benzothiazole, pentafluorobenzene, and 2-chlorothiophene remained unsuccessful.
  • 43
    • 79951839441 scopus 로고    scopus 로고
    • note
    • The KIE value was calculated by considering the partial H/D exchange reaction. The intermolecular KIE implies that C-H cleavage of 2-phenylpyridine would not be involved in the rate-determining step. See the Supporting Information for details.
  • 44
    • 2342527678 scopus 로고    scopus 로고
    • For reports of similar KIE values in palladium-catalyzed direct arylation and alkynylation through electrophilic C-H metalation, see: (a)
    • For reports of similar KIE values in palladium-catalyzed direct arylation and alkynylation through electrophilic C-H metalation, see: (a) Park, C.-H.; Ryabova, V.; Seregin, I. V.; Sromek, A. W.; Gevorgyan, V. Org. Lett. 2004, 6, 1159.
    • (2004) Org. Lett. , vol.6 , pp. 1159
    • Park, C.-H.1    Ryabova, V.2    Seregin, I.V.3    Sromek, A.W.4    Gevorgyan, V.5
  • 47
    • 26444441381 scopus 로고    scopus 로고
    • At this stage, the mechanism of C-H cleavage of phenylazines is not definitive. Thus, the pathway involving concerted metalation-deprotonation as well as σ-bond metathesis also could not be excluded. See: (a)
    • At this stage, the mechanism of C-H cleavage of phenylazines is not definitive. Thus, the pathway involving concerted metalation-deprotonation as well as σ-bond metathesis also could not be excluded. See: (a) Davies, D. L.; Donald, S. M. A.; Macgregor, S. A. J. Am. Chem. Soc. 2005, 127, 13754.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 13754
    • Davies, D.L.1    Donald, S.M.A.2    Macgregor, S.A.3
  • 52
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    • and references therein
    • (d) Lapointe, D.; Fagnou, K. Chem. Lett. 2010, 39, 1118 and references therein.
    • (2010) Chem. Lett. , vol.39 , pp. 1118
    • Lapointe, D.1    Fagnou, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.