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Volumn 29, Issue 18, 2010, Pages 4058-4065

Palladium(II)-catalyzed ortho arylation of 2-phenoxypyridines with potassium aryltrifluoroborates via C-H functionalization

Author keywords

[No Author keywords available]

Indexed keywords

ARYLATIONS; C-H BOND CLEAVAGE; C-H FUNCTIONALIZATION; CATALYTIC REACTIONS; EFFICIENT SYNTHESIS; KINETIC ISOTOPE EFFECTS; P-BENZOQUINONE; PALLADIUM ACETATE; RATE DETERMINING STEP; REDUCTIVE ELIMINATION; SODIUM METHOXIDE; TRANSMETALATION;

EID: 77956944281     PISSN: 02767333     EISSN: 15206041     Source Type: Journal    
DOI: 10.1021/om100494p     Document Type: Article
Times cited : (84)

References (84)
  • 70
    • 77956901573 scopus 로고    scopus 로고
    • Fresh p -benzoquinone through sublimation was used
    • Fresh p -benzoquinone through sublimation was used.
  • 71
    • 33645467565 scopus 로고    scopus 로고
    • Catalytic system of Pd(II)/DMSO, see:;, and references therein DMSO might slow catalyst decomposition and Pd(0) aggregation and further increase the product yield; see:; J. Am. Chem. Soc. 2007, 129, 11904-11905
    • Catalytic system of Pd(II)/DMSO, see: Steinhoff, B. A.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 4348-4355, and references therein DMSO might slow catalyst decomposition and Pd(0) aggregation and further increase the product yield; see: Hull, K. L.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 11904-11905
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 4348-4355
    • Steinhoff, B.A.1    Stahl, S.S.2    Hull, K.L.3    Sanford, M.S.4
  • 74
    • 77954846356 scopus 로고    scopus 로고
    • The yield of 2-(biphenyl-2-yloxy)pyridine (3a) in the reaction of 2-phenoxypyridine (1) with potassium phenyltrifluoroborate (2a) was determined to be 21%, 63%, 62%, and 12% in the presence of 0, 8, 16, and 32 equivalents of water, respectively. Trifluoroborate salts might undergo hydrolysis to afford boronic acids and further participate in the transmetalation-reductive elimination with palladacycle I. See:;;;;; DOI: 10.1002/anie.201001522
    • The yield of 2-(biphenyl-2-yloxy)pyridine (3a) in the reaction of 2-phenoxypyridine (1) with potassium phenyltrifluoroborate (2a) was determined to be 21%, 63%, 62%, and 12% in the presence of 0, 8, 16, and 32 equivalents of water, respectively. Trifluoroborate salts might undergo hydrolysis to afford boronic acids and further participate in the transmetalation-reductive elimination with palladacycle I. See: Bulters, M.; Harvey, J. M.; Jover, J.; Lennox, A; J. J.; Lloyd-Jones; G. C.; Murray, P. M. Angew. Chem., Int. Ed. DOI: 10.1002/anie.201001522.
    • Angew. Chem., Int. Ed.
    • Bulters, M.1    Harvey, J.M.2    Jover, J.3    Lennox, A.4    Lloyd-Jones, J.J.5    Murray, G.C.6
  • 76
    • 77956896957 scopus 로고    scopus 로고
    • Similar phenomena were observed by using the p -benzoquinone or olefin to promote transmetalation reductive elimination in the literature; see: References 4g and 6c
    • Similar phenomena were observed by using the p -benzoquinone or olefin to promote transmetalation reductive elimination in the literature; see: References 4g and 6c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.