메뉴 건너뛰기




Volumn 136, Issue 17, 2014, Pages 6453-6462

Cross-dehydrogenative couplings between indoles and β-keto esters: Ligand-assisted ligand tautomerization and dehydrogenation via a proton-assisted electron transfer to Pd(II)

Author keywords

[No Author keywords available]

Indexed keywords

DEHYDROGENATION; ELECTRON TRANSITIONS; ESTERIFICATION; ESTERS; ISOTOPES; PALLADIUM COMPOUNDS; POLYCYCLIC AROMATIC HYDROCARBONS; PROTONS;

EID: 84899767820     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja501681y     Document Type: Article
Times cited : (50)

References (46)
  • 1
    • 79952678116 scopus 로고    scopus 로고
    • For review of catalytic dehydrogenative cross-couplings, see
    • For review of catalytic dehydrogenative cross-couplings, see: Yeung, C. S.; Dong, V. M. Chem. Rev. 2011, 111, 1215
    • (2011) Chem. Rev. , vol.111 , pp. 1215
    • Yeung, C.S.1    Dong, V.M.2
  • 20
    • 84899708053 scopus 로고    scopus 로고
    • Ref 7.
    • Ref 7.
  • 34
    • 84899750076 scopus 로고    scopus 로고
    • 4 stationary points indicate that a proton and not a hydridic or radical H is transferred in the present hydrogen migration step, and therefore, we think the use of the PCET term is justified here (for details of population analysis, see the Supporting Information).
    • 4 stationary points indicate that a proton and not a hydridic or radical H is transferred in the present hydrogen migration step, and therefore, we think the use of the PCET term is justified here (for details of population analysis, see the Supporting Information).
  • 35
    • 79951617253 scopus 로고    scopus 로고
    • The identity of the catalyst resting state (i.e. the turnover-determining intermediate-see;) is uncertain. In the KIE calculations, it was assumed that the resting state does not involve 2a as the ligand. For more details about the KIE calculations, see the Supporting Information.
    • The identity of the catalyst resting state (i.e., the turnover-determining intermediate-see Kozuch, S.; Shaik, S. Acc. Chem. Res. 2011, 44, 101) is uncertain. In the KIE calculations, it was assumed that the resting state does not involve 2a as the ligand. For more details about the KIE calculations, see the Supporting Information.
    • (2011) Acc. Chem. Res. , vol.44 , pp. 101
    • Kozuch, S.1    Shaik, S.2
  • 36
  • 40
    • 0033997284 scopus 로고    scopus 로고
    • For a discussion of ligand effects on α-arylation of β-dicarbonyl compounds, see: ref 17c. The authors propose that bulky ligands assist in the reductive elimination step, but no mention is made of the ligand effects on the tautomerization step
    • Fox, J. M.; Huang, X.; Chieffi, A.; Buchwald, S. L. J. Am. Chem. Soc. 2000, 122, 1360 For a discussion of ligand effects on α-arylation of β-dicarbonyl compounds, see: ref 17c. The authors propose that bulky ligands assist in the reductive elimination step, but no mention is made of the ligand effects on the tautomerization step
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 1360
    • Fox, J.M.1    Huang, X.2    Chieffi, A.3    Buchwald, S.L.4
  • 45
    • 84878805142 scopus 로고    scopus 로고
    • We cannot rule out the involvement of dinuclear Pd(II) species in the C-C bond forming process. For an example of palladation in a dinuclear Pd(II) species, see
    • We cannot rule out the involvement of dinuclear Pd(II) species in the C-C bond forming process. For an example of palladation in a dinuclear Pd(II) species, see Sanhueza, I. A.; Wagner, A. M.; Sanford, M. S.; Schoenebeck, F. Chem. Sci. 2013, 4, 2767
    • (2013) Chem. Sci. , vol.4 , pp. 2767
    • Sanhueza, I.A.1    Wagner, A.M.2    Sanford, M.S.3    Schoenebeck, F.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.