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Volumn 73, Issue 19, 2008, Pages 7822-7825

Copper-catalyzed oxidative coupling of benzylic C-H bonds with 1,3-dicarbonyl compounds

Author keywords

[No Author keywords available]

Indexed keywords

ARSENIC COMPOUNDS; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; COPPER; HYDROGEN; ISOTOPES; NONMETALS;

EID: 53049104239     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801322p     Document Type: Article
Times cited : (94)

References (72)
  • 1
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    • For some recent reviews, see: a
    • For some recent reviews, see: (a) Godula, K.; Sames, D. Science 2006, 312, 67-72.
    • (2006) Science , vol.312 , pp. 67-72
    • Godula, K.1    Sames, D.2
  • 4
    • 33744510833 scopus 로고    scopus 로고
    • Dyker, G, Ed; Wiley-VCH: Weinheim
    • (d) Handbook of C-H Transformations; Dyker, G., Ed; Wiley-VCH: Weinheim, 2005.
    • (2005) Handbook of C-H Transformations
  • 9
    • 41149138082 scopus 로고    scopus 로고
    • For some representative examples and reviews, see: a
    • For some representative examples and reviews, see: (a) Ge, H.; Niphakis, M. J.; Georg, G. I. J. Am. Chem. Soc. 2008, 130, 3708-3709.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 3708-3709
    • Ge, H.1    Niphakis, M.J.2    Georg, G.I.3
  • 15
    • 40149110106 scopus 로고    scopus 로고
    • For some recent examples, see: a
    • For some recent examples, see: (a) Kim, H.; MacMillan, D. W. C. J. Am. Chem. Soc. 2008, 130, 398-399.
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 398-399
    • Kim, H.1    MacMillan, D.W.C.2
  • 49
    • 0001468409 scopus 로고
    • (d) Dyker, G. J. Org. Chem. 1993, 58, 6426-6428.
    • (1993) J. Org. Chem , vol.58 , pp. 6426-6428
    • Dyker, G.1
  • 50
    • 48849113342 scopus 로고    scopus 로고
    • For examples of intramolecular transition metal-catalyzed couplings of sp3 C-H bonds, see: (a) Watanabe, T, Oishi, S, Fujii, N, Ohno, H. Org. Lett. 2008, 10, 1759-1762
    • 3 C-H bonds, see: (a) Watanabe, T.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2008, 10, 1759-1762.
  • 60
    • 53049094438 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 62
    • 53049100067 scopus 로고    scopus 로고
    • 2. Use of tert-butylperoxyacetate gave slightly lower yields than tert-butylperoxybenzoate.
    • 2. Use of tert-butylperoxyacetate gave slightly lower yields than tert-butylperoxybenzoate.
  • 68
    • 49749219886 scopus 로고    scopus 로고
    • Kinetic deuterium isotope effects of 2.9 and 4.3 have previously been observed for the copper-catalyzed reaction of tert-butylperoxyesters with allylbenzene. The lower value observed here with ethylbenzene may be a result of a more linear H-transfer process, or an early transition state; see: (a) Denney, D. B.; Denney, D. Z.; Feig, G. Tetrahedron Lett. 1959, 15, 19-23.
    • Kinetic deuterium isotope effects of 2.9 and 4.3 have previously been observed for the copper-catalyzed reaction of tert-butylperoxyesters with allylbenzene. The lower value observed here with ethylbenzene may be a result of a more linear H-transfer process, or an early transition state; see: (a) Denney, D. B.; Denney, D. Z.; Feig, G. Tetrahedron Lett. 1959, 15, 19-23.
  • 72
    • 53049098219 scopus 로고    scopus 로고
    • Copper(II) perchlorate hexahydrate: $0.33 per gram (Aldrich). tert-Butylperoxybenzoate: $0.13 per gram (Aldrich).
    • Copper(II) perchlorate hexahydrate: $0.33 per gram (Aldrich). tert-Butylperoxybenzoate: $0.13 per gram (Aldrich).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.