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Volumn 4, Issue 21, 2002, Pages 3595-3598

Co(III)-alkyl complex- and Co(III)-alkylperoxo complex-catalyzed triethylsilylperoxidation of alkenes with molecular oxygen and triethylsilane

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ARTICLE;

EID: 0041807557     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0201299     Document Type: Article
Times cited : (117)

References (52)
  • 16
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    • A similar Co(II)-porphyrin complex-catalyzed peroxygenation in 2-propanol leading to the corresponding hydroperoxide has been also reported by Sugamoto and co-workers: Sugamoto, K.; Matsushita, Y.; Matsui, T. J. Chem. Soc., Perkin Trans. 1 1998, 3989. Furthermore, Magnus and co-workers reported the Mn(III) complex-catalyzed hydroperoxidation of alkenes in the presence of phenylsilane under an oxygen atmosphere: Magnus, P.; Scott, D. A.; Fielding, M. R. Tetrahedron Lett. 2001, 42, 4127.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 3989
    • Sugamoto, K.1    Matsushita, Y.2    Matsui, T.3
  • 17
    • 0035908267 scopus 로고    scopus 로고
    • A similar Co(II)-porphyrin complex-catalyzed peroxygenation in 2-propanol leading to the corresponding hydroperoxide has been also reported by Sugamoto and co-workers: Sugamoto, K.; Matsushita, Y.; Matsui, T. J. Chem. Soc., Perkin Trans. 1 1998, 3989. Furthermore, Magnus and co-workers reported the Mn(III) complex-catalyzed hydroperoxidation of alkenes in the presence of phenylsilane under an oxygen atmosphere: Magnus, P.; Scott, D. A.; Fielding, M. R. Tetrahedron Lett. 2001, 42, 4127.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4127
    • Magnus, P.1    Scott, D.A.2    Fielding, M.R.3
  • 23
    • 0041769284 scopus 로고
    • Foote, S., Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Chapman & Hall: New York, Chapter 5
    • Dussault, P. H. In Active Oxygen in Chemistry; Foote, S., Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Chapman & Hall: New York, 1995; Chapter 5.
    • (1995) Active Oxygen in Chemistry
    • Dussault, P.H.1
  • 24
    • 0042771135 scopus 로고
    • Ando, W., Ed.; Wiley: New York, Chapter 2
    • Porter, N. A. In Organic Peroxides: Ando, W., Ed.; Wiley: New York, 1992; Chapter 2.
    • (1992) Organic Peroxides
    • Porter, N.A.1
  • 25
    • 0041769289 scopus 로고    scopus 로고
    • note
    • Representative Reaction Conditions. Into a two-neck 50 mL flask, charged with dioxygen, was added a mixture of alkene (2 mmol) and cobalt-(II) complex (0.10 mmol) in 1,2-dichloroethane (DCE) (5 mL). Then, triethylsilane (4 mmol) was added via a 1.0 mL gaslight syringe, and the reaction mixture was stirred vigorously under an oxygen atmosphere at room temperature.
  • 26
    • 0042771134 scopus 로고    scopus 로고
    • note
    • In all cases, the resulting triethylsilyl peroxide could not be separated from the remaining alkene. Therefore, after treatment of this mixture with one portion of concentrated HCl in MeOH, the peroxide was isolated in the form of the corresponding hydroperoxide.
  • 29
    • 0042269950 scopus 로고    scopus 로고
    • note
    • Conversion in the complex 4-catalyzed peroxidation was much lower than that in the conventional Co(II)-catalyzed reaction, which would be due to the stabilization of complex 4 by the coordinated pyridine as a sixth ligand.
  • 31
    • 0042269944 scopus 로고    scopus 로고
    • note
    • 2 In the present reaction, however, no product derived from such an insertion reaction was observed.
  • 32
    • 0001639833 scopus 로고    scopus 로고
    • and references therein
    • Analogous metal-exchange reactions of tin alkoxides and copper-(I) alkoxides with silane are known: (a) Hays, D. S.; Scholl, M.; Fu, G. C. J. Org. Chem. 1996, 61, 6751 and references therein.
    • (1996) J. Org. Chem. , vol.61 , pp. 6751
    • Hays, D.S.1    Scholl, M.2    Fu, G.C.3
  • 42
    • 0042269949 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Willey-VCH: Weinheim, Germany, Chapter 1.8
    • (b) Iqbal, J.; Sanghi, R.; Nandy, J. P. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Willey-VCH: Weinheim, Germany, 2001; Chapter 1.8.
    • (2001) Radicals in Organic Synthesis
    • Iqbal, J.1    Sanghi, R.2    Nandy, J.P.3
  • 44
    • 0041769288 scopus 로고    scopus 로고
    • note
    • 3SiOOH at the first step and the following addition to the alkene is not important in the Isayama-Mukaiyama reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.