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Volumn 12, Issue 3, 2010, Pages 532-535

O-acetyl oximes as transformable directing groups for Pd-catalyzed C-H bond functionalization

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; OXIME; PALLADIUM;

EID: 75749134825     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902720d     Document Type: Article
Times cited : (179)

References (48)
  • 16
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    • For reviews on ketone-directed C-H alkylation and arylation reactions catalyzed by metals other than Pd, see: (a) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
    • (2007) Chem. Rev. , vol.107 , pp. 174
    • Alberico, D.1    Scott, M.E.2    Lautens, M.3
  • 17
    • 77349090183 scopus 로고    scopus 로고
    • Online early access. DOI: 10.1021/ cr900005n. Published Online: May 13, accessed December 10, 2009.
    • (b) Colby, D. A.; Bergman, R. G.; Ellman, J. A. Chem. Rev. [Online early access]. DOI: 10.1021/ cr900005n. Published Online: May 13, 2009. http://pubs.acs.org/doi/pdf/10.1021/cr900005n (accessed December 10, 2009).
    • (2009) Chem. Rev.
    • Colby, D.A.1    Bergman, R.G.2    Ellman, J.A.3
  • 22
    • 25444475266 scopus 로고    scopus 로고
    • For related C-H acetoxylation reactions of other substrates, see: (a) Kalyani, D.; Sanford, M. S. Org. Lett. 2005, 7, 4149.
    • (2005) Org. Lett. , vol.7 , pp. 4149
    • Kalyani, D.1    Sanford, M.S.2
  • 30
    • 0027197194 scopus 로고
    • Conversion of oxime ethers to ketones has been reported using Amberlyst 15 at temperatures ranging from 25 to 110 °C. See: (a) Sakamoto, T.; Kikugawa, Y. Synthesis 1993, 563.
    • (1993) Synthesis , vol.563
    • Sakamoto, T.1    Kikugawa, Y.2
  • 31
    • 0034619262 scopus 로고    scopus 로고
    • 3250. Inourhands, 2andderivativeswereunreactive- thereportedconditionsatroomtemperature. Atelevatedtemperatures(80°C), 2reacted-formacomplexmixtureofproductsthatdidnotincludetheexpectedβ- acetoxyorβ-hydroxyketone
    • (b) Mears, R. J.; Sailes, H. E.; Watts, J. P.; Whiting, A. J. Chem. Soc., Perkin Trans. 1 2000, 3250. In our hands, 2 and derivatives were unreactive to the reported conditions at room temperature. At elevated temperatures (80 °C), 2 reacted to form a complex mixture of products that did not include the expected β-acetoxy or β-hydroxy ketone.
    • (2000) J. Chem. Soc., Perkin Trans. , vol.1
    • Mears, R.J.1    Sailes, H.E.2    Watts, J.P.3    Whiting, A.4
  • 32
    • 75749144343 scopus 로고    scopus 로고
    • Palladium-Catalyzed Functionalization of C-H Bonds and Alkenes. Ph.D. Thesis, University of Michigan, April
    • (a) Desai, L. V. Palladium-Catalyzed Functionalization of C-H Bonds and Alkenes. Ph.D. Thesis, University of Michigan, April 2008.
    • (2008)
    • Desai, L.V.1
  • 38
    • 0004079266 scopus 로고    scopus 로고
    • Cost calculated on a molar basis using: Aldrich Chemical: Milwaukee, WI
    • Cost calculated on a molar basis using: Aldrich Catalog Handbook of Fine Chemicals; Aldrich Chemical: Milwaukee, WI, 2009.
    • (2009) Aldrich Catalog Handbook of Fine Chemicals
  • 40
    • 75749104739 scopus 로고    scopus 로고
    • The acetoxylated products were typically isolated as mixtures of EIZ oxime stereoisomers, which rapidly interconvert under the catalytic reaction conditions
    • The acetoxylated products were typically isolated as mixtures of EIZ oxime stereoisomers, which rapidly interconvert under the catalytic reaction conditions.
  • 41
    • 84970581388 scopus 로고
    • For an example under similar conditions, see: Waring, P. Aust. J. Chem. 1988, 41, 667.
    • (1988) Aust. J. Chem. , vol.41 , pp. 667
    • Waring, P.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.