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Volumn 130, Issue 25, 2008, Pages 7824-7825

Cu-facilitated C-O bond formation using N-hydroxyphthalimide: Efficient and selective functionalization of benzyl and allylic C-H bonds

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; COPPER; HYDROCARBON; N HYDROXYPHTHALIMIDE; PHTHALIMIDE DERIVATIVE;

EID: 45749083802     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja8031218     Document Type: Article
Times cited : (147)

References (33)
  • 11
    • 3242790166 scopus 로고    scopus 로고
    • For a previous example on the combined use of NHPl and CuCl cocatalysts for aerobic oxidation of benzylic compounds, see: Nechab, M, Einhorn, C, Einhorn, J. Chem. Commun. 2004, 1500
    • For a previous example on the combined use of NHPl and CuCl cocatalysts for aerobic oxidation of benzylic compounds, see: Nechab, M.; Einhorn, C.; Einhorn, J. Chem. Commun. 2004, 1500.
  • 12
    • 45749135053 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 13
    • 45749133032 scopus 로고    scopus 로고
    • The following oxidants were also tested without success: tert-butylperoxide, Dess-Martin periodate, bis(trifluoroacetate) iodobenzene, iodosobenzene, Oxone, and 1,4-benzoquinone. See the Supporting Information for details.
    • The following oxidants were also tested without success: tert-butylperoxide, Dess-Martin periodate, bis(trifluoroacetate) iodobenzene, iodosobenzene, Oxone, and 1,4-benzoquinone. See the Supporting Information for details.
  • 24
    • 0000828619 scopus 로고    scopus 로고
    • In fact, it was reported that the presence of Co(II) catalysts in the NHPI-catalyzed aerobic oxidation of alkanes can reduce the induction period and, therefore, enhancing the subsequent radical propagation steps: Ishii, Y, Iwahama, T, Sakaguchi, S, Nakayama, K, Nishiyama, Y. J. Org. Chem. 1996, 61, 4520
    • In fact, it was reported that the presence of Co(II) catalysts in the NHPI-catalyzed aerobic oxidation of alkanes can reduce the induction period and, therefore, enhancing the subsequent radical propagation steps: Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Nishiyama, Y. J. Org. Chem. 1996, 61, 4520.
  • 25
    • 33846128749 scopus 로고    scopus 로고
    • Recently, the Cu-catalyzed amidation of benzylic and allylic C-H bonds was reported, suggesting a stepwise pathway via an acetate intermediate: Pelletier, G.; Powell, D. A. Org. Lett. 2006, 8, 6031.
    • Recently, the Cu-catalyzed amidation of benzylic and allylic C-H bonds was reported, suggesting a stepwise pathway via an acetate intermediate: Pelletier, G.; Powell, D. A. Org. Lett. 2006, 8, 6031.
  • 28
    • 45749138800 scopus 로고    scopus 로고
    • Espenson et al. observed the recombination between PINO with p-xylene radical, although no product yields were presented (ref 10).
    • Espenson et al. observed the recombination between PINO with p-xylene radical, although no product yields were presented (ref 10).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.