메뉴 건너뛰기




Volumn 137, Issue 26, 2015, Pages 8556-8563

Ligand-Controlled Palladium-Catalyzed Alkoxycarbonylation of Allenes: Regioselective Synthesis of α,β- and β,γ-Unsaturated Esters

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHELATION; ESTERIFICATION; ESTERS; HYDROCARBONS; LIGANDS; PALLADIUM;

EID: 84936797553     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b04052     Document Type: Article
Times cited : (71)

References (81)
  • 1
    • 35048883596 scopus 로고    scopus 로고
    • Catalytic Carbonylation Reactions
    • In; Springer: Berlin.
    • Catalytic Carbonylation Reactions. In Catalytic Carbonylation Reactions; Beller, M., Ed.; Springer: Berlin, 2006.
    • (2006) Catalytic Carbonylation Reactions
    • Beller, M.1
  • 2
    • 77954786152 scopus 로고    scopus 로고
    • Wiley-VCH Verlag GmbH: Weinheim.
    • Modern Carbonylation Methods; Wiley-VCH Verlag GmbH: Weinheim, 2008.
    • (2008) Modern Carbonylation Methods
  • 7
    • 0035498330 scopus 로고    scopus 로고
    • Kiss, G. Chem. Rev. 2001, 101, 3435-3456
    • (2001) Chem. Rev. , vol.101 , pp. 3435-3456
    • Kiss, G.1
  • 16
    • 84890988149 scopus 로고    scopus 로고
    • Carbonylation of Alkenes and Dienes
    • In; Wiley-VCH Verlag GmbH: Weinheim
    • Kégl, T. Carbonylation of Alkenes and Dienes. In Modern Carbonylation Methods; Wiley-VCH Verlag GmbH: Weinheim, 2008; pp 161-198.
    • (2008) Modern Carbonylation Methods , pp. 161-198
    • Kégl, T.1
  • 25
    • 84890989088 scopus 로고    scopus 로고
    • Recent Developments in Alkyne Carbonylation
    • In; Wiley-VCH Verlag GmbH: Weinheim
    • Doherty, S.; Knight, J. G.; Smyth, C. H. Recent Developments in Alkyne Carbonylation. In Modern Carbonylation Methods; Wiley-VCH Verlag GmbH: Weinheim, 2008; pp 251-290.
    • (2008) Modern Carbonylation Methods , pp. 251-290
    • Doherty, S.1    Knight, J.G.2    Smyth, C.H.3
  • 38
    • 4544320494 scopus 로고    scopus 로고
    • Wiley-VCH Verlag GmbH: Weinheim.
    • Modern Allene Chemistry; Wiley-VCH Verlag GmbH: Weinheim, 2008.
    • (2008) Modern Allene Chemistry
  • 45
    • 4544320494 scopus 로고    scopus 로고
    • Fundamentals and Application of Free Radical Addition to Allenes
    • In; Wiley-VCH Verlag GmbH: Weinheim
    • Hartung, J.; Kopf, T. Fundamentals and Application of Free Radical Addition to Allenes. In Modern Allene Chemistry; Wiley-VCH Verlag GmbH: Weinheim, 2008; pp 701-726.
    • (2008) Modern Allene Chemistry , pp. 701-726
    • Hartung, J.1    Kopf, T.2
  • 55
    • 33746062487 scopus 로고    scopus 로고
    • Cyclizations of Allenes
    • In; Wiley-VCH Verlag GmbH: Weinheim
    • Tius, M. A. Cyclizations of Allenes. In Modern Allene Chemistry; Wiley-VCH Verlag GmbH: Weinheim, 2008; pp 817-845.
    • (2008) Modern Allene Chemistry , pp. 817-845
    • Tius, M.A.1
  • 57
    • 34748870174 scopus 로고    scopus 로고
    • Oxidation of Allenes
    • In; Wiley-VCH Verlag GmbH: Weinheim
    • Horváth, A.; Bäckvall, J.-E. Oxidation of Allenes. In Modern Allene Chemistry; Wiley-VCH Verlag GmbH: Weinheim, 2008; pp 973-994.
    • (2008) Modern Allene Chemistry , pp. 973-994
    • Horváth, A.1    Bäckvall, J.-E.2
  • 67
    • 71149100739 scopus 로고    scopus 로고
    • Carbonylation of Allenes
    • In; Wiley-VCH Verlag GmbH: Weinheim
    • Nomoto, A.; Ogawa, A. Carbonylation of Allenes. In Modern Carbonylation Methods; Wiley-VCH Verlag GmbH: Weinheim, 2008; pp 291-300.
    • (2008) Modern Carbonylation Methods , pp. 291-300
    • Nomoto, A.1    Ogawa, A.2
  • 68
    • 84903491107 scopus 로고    scopus 로고
    • 4.18 Hydroformylation and Related Carbonylation Reactions of Alkenes, Alkynes, and Allenes
    • In, 2 nd ed. Knochel, P. Elsevier: Amsterdam
    • Breit, B.; Diab, L. 4.18 Hydroformylation and Related Carbonylation Reactions of Alkenes, Alkynes, and Allenes. In Comprehensive Organic Synthesis II, 2 nd ed.; Knochel, P., Ed.; Elsevier: Amsterdam, 2014; pp 995-1053.
    • (2014) Comprehensive Organic Synthesis II , pp. 995-1053
    • Breit, B.1    Diab, L.2
  • 77
    • 9644257457 scopus 로고    scopus 로고
    • Coordination Polymerization of Dienes, Allenes, and Methylenecycloalkanes
    • Although the conversion of 1a is nearly 100%, the yield of product was only 70%. Apart from the corresponding isomer 3a (7% yield, detected by GC), the other by-product was not observed from GC. We think allene is polymerized or decomposed under the reaction conditions. For the related polymerization of allenes, see: In; Springer: Berlin, Vol.
    • Although the conversion of 1a is nearly 100%, the yield of product was only 70%. Apart from the corresponding isomer 3a (7% yield, detected by GC), the other by-product was not observed from GC. We think allene is polymerized or decomposed under the reaction conditions. For the related polymerization of allenes, see: Osakada, K.; Takeuchi, D. Coordination Polymerization of Dienes, Allenes, and Methylenecycloalkanes. In Polymer Synthesis; Springer: Berlin, 2004; Vol. 171, pp 137-194.
    • (2004) Polymer Synthesis , vol.171 , pp. 137-194
    • Osakada, K.1    Takeuchi, D.2
  • 78
    • 0038584673 scopus 로고
    • The ligands and counterions effect for the regioselectivity control of allene insertion into Pd-H bond cannot be completely clarified in the current work. For the research on the effect of counterions and monodentate and bidentate ligands on alkene insertion regioselectivity, see
    • The ligands and counterions effect for the regioselectivity control of allene insertion into Pd-H bond cannot be completely clarified in the current work. For the research on the effect of counterions and monodentate and bidentate ligands on alkene insertion regioselectivity, see: Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7
    • (1995) Acc. Chem. Res. , vol.28 , pp. 2-7
    • Cabri, W.1    Candiani, I.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.