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Volumn 10, Issue 5, 2008, Pages 803-805

C-H bond oxidation initiated pummerer- And knoevenagel-Type reactions of benzyl sulfide and 1,3-dicarbonyl compounds

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EID: 51549110492     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol702934k     Document Type: Article
Times cited : (102)

References (26)
  • 1
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    • (a) Bergman, R. G. Nature 2007, 446, 391.
    • (2007) Nature , vol.446 , pp. 391
    • Bergman, R.G.1
  • 3
    • 33744510833 scopus 로고    scopus 로고
    • Dyker, D, Ed, Wiley-VCH: Weinheim
    • (c) Handbook of C-H Transformations; Dyker, D., Ed.; Wiley-VCH: Weinheim, 2005.
    • (2005) Handbook of C-H Transformations
  • 4
    • 9944258407 scopus 로고    scopus 로고
    • For representative reviews, see: a
    • For representative reviews, see: (a) Crabtree, R. H. J. Organomet. Chem. 2004, 689, 4083.
    • (2004) J. Organomet. Chem , vol.689 , pp. 4083
    • Crabtree, R.H.1
  • 17
    • 33645461780 scopus 로고    scopus 로고
    • DDQ-mediated C-H bond activation was reported: Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242.
    • DDQ-mediated C-H bond activation was reported: Zhang, Y.; Li, C.-J. J. Am. Chem. Soc. 2006, 128, 4242.
  • 21
    • 12344302489 scopus 로고    scopus 로고
    • An alternative method for generation of the thionium precursor, hemithioacetal. is based on the addition of thiols to glyoxamide; see: McAllister, L. A, McCormick, R. A, Brand, S, Procter, D. J. Angew. Chem, Int. Ed. 2005, 44, 452
    • An alternative method for generation of the thionium precursor, hemithioacetal. is based on the addition of thiols to glyoxamide; see: McAllister, L. A.; McCormick, R. A.; Brand, S.; Procter, D. J. Angew. Chem., Int. Ed. 2005, 44, 452.
  • 22
    • 58149198179 scopus 로고    scopus 로고
    • No desired product was obtained when p-fluoranil, p-chloranil. and p-bromanil were used as oxidants under the same reaction conditions
    • No desired product was obtained when p-fluoranil, p-chloranil. and p-bromanil were used as oxidants under the same reaction conditions.
  • 23
    • 58149193827 scopus 로고    scopus 로고
    • One of possibilities of C H bond oxidation is initiated by single electron transfer from sulfur to quinone; see: Gorner. H. Pholochem. Photobiol. 2006, 82, 71
    • One of possibilities of C H bond oxidation is initiated by single electron transfer from sulfur to quinone; see: Gorner. H. Pholochem. Photobiol. 2006, 82, 71.
  • 24
    • 4644339111 scopus 로고    scopus 로고
    • This step is reversible. Compound 3e was obtained as a major product by the reaction of 3d and 2b. Oxidative cleavage benzylic C-C bonds assisted by heteroatoms: Wang, L, Seiders, J. R, II; Floreancig, P. E. J. Am. Chem. Soc. 2004, 126. 12596
    • This step is reversible. Compound 3e was obtained as a major product by the reaction of 3d and 2b. Oxidative cleavage benzylic C-C bonds assisted by heteroatoms: Wang, L.; Seiders, J. R., II; Floreancig, P. E. J. Am. Chem. Soc. 2004, 126. 12596.
  • 25
    • 33646900271 scopus 로고    scopus 로고
    • Compound 3a was transformed into 4b in 93% isolated yield at 100°C for 8 h in the presence of 2 equiv of o-chloranil. For related examples of C-S bond cleavage, see: (a) Baciocchi, E.; Del, Giacco, T.; Giombolini, P.; Lanzalunga, O. Tetrahedron 2006, 62, 6566.
    • Compound 3a was transformed into 4b in 93% isolated yield at 100°C for 8 h in the presence of 2 equiv of o-chloranil. For related examples of C-S bond cleavage, see: (a) Baciocchi, E.; Del, Giacco, T.; Giombolini, P.; Lanzalunga, O. Tetrahedron 2006, 62, 6566.


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