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Abstract:
Heterocyclic ketene N,N-acetals are versatile building blocks for the synthesis of nitrogen-containing heterocyclic compounds. In the present work, the anodic oxidation of catechols 2a-f in the presence of alpha-oxoheterocychc ketene N,N-acetals 1a-d has been investigated using cyclic voltammetry and controlled-potential electrolysis methods. These results indicate that alpha-oxoheterocyclic ketene N,N-acetals could undergo Michael addition to the anodically generated o-benzo-quinones and produce alpha-carbon-arylated products in good yields. This approach provides effective and "green" access to the synthesis of alpha-aryl alpha-oxoheterocyclic ketene N,N-acetals containing an electron-rich aromatic ring. In addition, density functional theory calculations were performed to explain the exclusive formation of alpha-carbon-arylated products. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN: 1434-193X
Year: 2009
Issue: 33
Volume: 2009
Page: 5832-5840
2 . 8 0 0
JCR@2022
ESI Discipline: CHEMISTRY;
JCR Journal Grade:2
CAS Journal Grade:1
Cited Count:
WoS CC Cited Count: 12
SCOPUS Cited Count: 15
ESI Highly Cited Papers on the List: 0 Unfold All
WanFang Cited Count:
Chinese Cited Count:
30 Days PV: 3
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