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Volumn 133, Issue 37, 2011, Pages 14566-14569

Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICALLY ACTIVE COMPOUNDS; CYCLIC KETONES; CYCLOHEXANONES; UNSATURATED CARBONYL COMPOUNDS;

EID: 80052802032     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja206575j     Document Type: Article
Times cited : (329)

References (61)
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    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 119-149
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  • 23
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    • For a method employing catalytic 2-iodoxybenzene sulfonate (IBS) in combination stoichiometric Oxone see
    • For a method employing catalytic 2-iodoxybenzene sulfonate (IBS) in combination stoichiometric Oxone, see: Uyanik, M.; Akakura, M.; Ishihara, K. J. Am. Chem. Soc. 2009, 131, 251
    • (2009) J. Am. Chem. Soc. , vol.131 , pp. 251
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  • 25
    • 84907686893 scopus 로고    scopus 로고
    • 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
    • In; John Wiley & Sons, Inc. New York
    • Buckle, D. R. 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone. In Encyclopedia of Reagents for Organic Synthesis; John Wiley & Sons, Inc.: New York, 2010.
    • (2010) Encyclopedia of Reagents for Organic Synthesis
    • Buckle, D.R.1
  • 33
    • 77954248100 scopus 로고    scopus 로고
    • For a recent review of reactions of this type, see
    • For a recent review of reactions of this type, see: Muzart, J. Eur. J. Org. Chem. 2010, 3779
    • (2010) Eur. J. Org. Chem. , pp. 3779
    • Muzart, J.1
  • 36
    • 79953863843 scopus 로고    scopus 로고
    • 2 acceptor. Other cyclohexanone substrates lacking gem -disubstitution undergo stoichiometric deydrogenation, forming an Ir-phenoxide product
    • 2 acceptor. Other cyclohexanone substrates lacking gem -disubstitution undergo stoichiometric deydrogenation, forming an Ir-phenoxide product. Zhang, X. W.; Wang, D. Y.; Emge, T. J.; Goldman, A. S. Inorg. Chim. Acta 2011, 369, 253
    • (2011) Inorg. Chim. Acta , vol.369 , pp. 253
    • Zhang, X.W.1    Wang, D.Y.2    Emge, T.J.3    Goldman, A.S.4
  • 37
    • 0011500587 scopus 로고
    • The mechanism could proceed via C - and/or O -bound Pd enolates, although β-hydride elimination is expected to occur from the C -bound enolate. For the formation of a C -bound Pd-enolate under relatively similar conditions, see
    • The mechanism could proceed via C-and/or O -bound Pd enolates, although β-hydride elimination is expected to occur from the C -bound enolate. For the formation of a C -bound Pd-enolate under relatively similar conditions, see: Fuchita, Y.; Harada, Y. Inorg. Chim. Acta 1993, 208, 43
    • (1993) Inorg. Chim. Acta , vol.208 , pp. 43
    • Fuchita, Y.1    Harada, Y.2
  • 40
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    • 2 disproportionation under related conditions, see the Supporting Information for the following reference
    • 2 disproportionation under related conditions, see the Supporting Information for the following reference: Steinhoff, B. A.; Fix, S. R.; Stahl, S. S. J. Am. Chem. Soc. 2002, 124, 766
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 766
    • Steinhoff, B.A.1    Fix, S.R.2    Stahl, S.S.3
  • 46
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    • For mechanistic characterization of this catalyst system, see
    • For mechanistic characterization of this catalyst system, see: Steinhoff, B. A.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 4348
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 4348
    • Steinhoff, B.A.1    Stahl, S.S.2
  • 61
    • 77954602413 scopus 로고    scopus 로고
    • Dehydrogenation of substrate 1 has been carried out on a 10-g scale using a prototype flow reactor donated to UW-Madison by Eli Lilly. See Supporting Information and the following reference for details
    • Dehydrogenation of substrate 1 has been carried out on a 10-g scale using a prototype flow reactor donated to UW-Madison by Eli Lilly. See Supporting Information and the following reference for details: Ye, X.; Johnson, M. D.; Diao, T.; Yates, M. H.; Stahl, S. S. Green Chem. 2010, 12, 1180
    • (2010) Green Chem. , vol.12 , pp. 1180
    • Ye, X.1    Johnson, M.D.2    Diao, T.3    Yates, M.H.4    Stahl, S.S.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.