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Volumn 135, Issue 32, 2013, Pages 12122-12134

Radical-based regioselective C-H functionalization of electron-deficient heteroarenes: Scope, tunability, and predictability

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICALLY ACTIVE MOLECULES; C-H FUNCTIONALIZATION; ELECTRON-DEFICIENT; FUNCTIONALIZATIONS; ISOPROPYL GROUPS; RADICAL FUNCTIONALIZATION; REACTION CONDITIONS; RELATIVE CONTRIBUTION;

EID: 84882263695     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja406223k     Document Type: Article
Times cited : (279)

References (83)
  • 1
    • 84868375511 scopus 로고    scopus 로고
    • Wiley: Chichester
    • For an overview of standard functionalization methods, see: Joule, J. A.; Mills, K. Heterocyclic Chemistry, 5 th ed; Wiley: Chichester, 2010.
    • (2010) Heterocyclic Chemistry
    • Joule, J.A.1    Mills, K.2
  • 30
    • 77956199653 scopus 로고    scopus 로고
    • For a comprehensive review of the Minisci reaction, which is the most widely studied system, see: Punta, C.; Minisci, F. Trends Heterocycl. Chem. 2008, 13, 1-68
    • (2008) Trends Heterocycl. Chem. , vol.13 , pp. 1-68
    • Punta, C.1    Minisci, F.2
  • 37
    • 49149135741 scopus 로고
    • Palla, G. Tetrahedron 1981, 37, 2917-2919
    • (1981) Tetrahedron , vol.37 , pp. 2917-2919
    • Palla, G.1
  • 42
    • 84882282912 scopus 로고
    • Viehe, H. G. Janousek, Z. Merényi, R. D. Reidel Publishing Company: Louvain-la-Neuve, Belgium
    • Tiecco, M. In NATO Advanced Research Workshop on Substituent Effects in Radical Chemistry; Viehe, H. G.; Janousek, Z.; Merényi, R., Eds.; D. Reidel Publishing Company: Louvain-la-Neuve, Belgium, 1986; Vol. 189, p 435-442
    • (1986) NATO Advanced Research Workshop on Substituent Effects in Radical Chemistry , vol.189 , pp. 435-442
    • Tiecco, M.1
  • 44
    • 77956696881 scopus 로고
    • For an example of radical methylation of 3-picoline showing a strong preference for C2 substitution, see: Abramovitch, R. A.; Kenaschuk, K. Can. J. Chem. 1967, 45, 509-513
    • (1967) Can. J. Chem. , vol.45 , pp. 509-513
    • Abramovitch, R.A.1    Kenaschuk, K.2
  • 45
    • 0345359241 scopus 로고    scopus 로고
    • For an example of substituent effects in the Minisci alkylation of unsymmetrical 3,6-disubstituted pyridines, see: Cowden, C. J. Org. Lett. 2003, 5, 4497-4499
    • (2003) Org. Lett. , vol.5 , pp. 4497-4499
    • Cowden, C.J.1
  • 46
    • 0042810206 scopus 로고
    • Studies into the regioselectivity of radical substitution of arenes has also shown substituent effects, see: Shelton, J. R.; Uzelmeier, C. W. J. Am. Chem. Soc. 1966, 88, 5222-5228
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 5222-5228
    • Shelton, J.R.1    Uzelmeier, C.W.2
  • 50
    • 84882261140 scopus 로고    scopus 로고
    • we thank a referee for this suggestion
    • we thank a referee for this suggestion.
  • 52
    • 0002271475 scopus 로고
    • Viehe, H. G. Janousek, Z. Merényi, R. D. Reidel Publishing Company: Louvain-la-Neuve, Belgium
    • Minisci, F. In NATO Advanced Research Workshop on Substituent Effects in Radical Chemistry; Viehe, H. G.; Janousek, Z.; Merényi, R., Eds.; D. Reidel Publishing Company: Louvain-la-Neuve, Belgium, 1986; Vol. 189, p 391-434.
    • (1986) NATO Advanced Research Workshop on Substituent Effects in Radical Chemistry , vol.189 , pp. 391-434
    • Minisci, F.1
  • 56
    • 0000699506 scopus 로고    scopus 로고
    • The ionization potential of trifluoromethyl radical is reported as 9.05 eV in Asher, R. L.; Ruscic, B. J. Chem. Phys. 1997, 106, 210-221
    • (1997) J. Chem. Phys. , vol.106 , pp. 210-221
    • Asher, R.L.1    Ruscic, B.2
  • 61
    • 9544255986 scopus 로고
    • For a clear example of the impact of steric effects on the regioselectivity of the Minisci reaction, see: Pfleger, K.; Fuchs, W.; Pailer, M. Monatsh. Chem. 1978, 109, 597-602
    • (1978) Monatsh. Chem. , vol.109 , pp. 597-602
    • Pfleger, K.1    Fuchs, W.2    Pailer, M.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.