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Volumn 12, Issue 15, 2010, Pages 3414-3417

Facile benzo-ring construction via palladium-catalyzed functionalization of unactivated sp3 C-H bonds under mild reaction conditions

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Indexed keywords


EID: 77955147864     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101220x     Document Type: Article
Times cited : (142)

References (65)
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    • C-H activation in synthesis
    • C-H activation in synthesis
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    • C-H insertion via nitrene and carbene
    • C-H insertion via nitrene and carbene
  • 10
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    • 3 C-H bonds
    • 3 C-H bonds
  • 11
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    • Dyker, G., Ed. Wily-VCH: Weinheim, Germany
    • Dyker, G., Ed. Handbook of C-H Transformation; Wily-VCH: Weinheim, Germany, 2005; Vols. 1-3.
    • (2005) Handbook of C-H Transformation , vol.13
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    • Bergman, R. G. Nature 2007, 446, 391-393
    • (2007) Nature , vol.446 , pp. 391-393
    • Bergman, R.G.1
  • 21
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    • Directed C-H activation
    • Directed C-H activation
  • 39
    • 33746872900 scopus 로고    scopus 로고
    • A palladacycle intermediate was isolated and characterized
    • Reddy, B. V. S.; Reddy, L. R.; Corey, E. J. Org. Lett. 2006, 8, 3391-3394 A palladacycle intermediate was isolated and characterized.
    • (2006) Org. Lett. , vol.8 , pp. 3391-3394
    • Reddy, B.V.S.1    Reddy, L.R.2    Corey, E.J.3
  • 41
    • 77955168843 scopus 로고    scopus 로고
    • Pd(IV) chemistry
    • Pd(IV) chemistry
  • 47
    • 77955155999 scopus 로고    scopus 로고
    • The original condition was 110-130 °C in neat condition with 1.5 equiv of AgOAc. A newer condition without Ag salt at 90 °C was recently reported (ref 8c). Although many C-H activations in AcOH and TFA have been developed, neutral and low boiling point solvents are more favorable for practical synthesis
    • The original condition was 110-130 °C in neat condition with 1.5 equiv of AgOAc. A newer condition without Ag salt at 90 °C was recently reported (ref 8c). Although many C-H activations in AcOH and TFA have been developed, neutral and low boiling point solvents are more favorable for practical synthesis.
  • 55
    • 77955150041 scopus 로고    scopus 로고
    • 2O) data compiled by R. Wiliams
    • 2O) data compiled by R. Wiliams.
  • 56
    • 77955159205 scopus 로고    scopus 로고
    • See discussion on proton shuttle in ref 14a
    • See discussion on proton shuttle in ref 14a.
  • 57
    • 77955150263 scopus 로고    scopus 로고
    • 2 is added to prevent t-BuOH from freezing
    • 2 is added to prevent t-BuOH from freezing.
  • 58
    • 77955144464 scopus 로고    scopus 로고
    • Higher yield (60-80%) can be achieved with AcOH or PivOH at 110°C
    • Higher yield (60-80%) can be achieved with AcOH or PivOH at 110°C.
  • 59
    • 77955149575 scopus 로고    scopus 로고
    • 3 C-H bonds at room temperature
    • 3 C-H bonds at room temperature
  • 60
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    • ref 3f
    • ref 3f.
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    • IV intermediate, and the dissociation for oxidative addition has not been discussed. See
    • IV intermediate, and the dissociation for oxidative addition has not been discussed. See: Racowski, J. M.; Dick, A. R.; Sanford, M. S. J. Am. Chem. Soc. 2009, 131, 10974-10983
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 10974-10983
    • Racowski, J.M.1    Dick, A.R.2    Sanford, M.S.3
  • 64
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    • II/IV oxidative addition
    • II/IV oxidative addition.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.