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Author:

Zeng, Cheng-Chu (Zeng, Cheng-Chu.) (Scholars:曾程初) | Ping, Da-Wei (Ping, Da-Wei.) | Xu, Yi-Sheng (Xu, Yi-Sheng.) | Hu, Li-Ming (Hu, Li-Ming.) (Scholars:胡利明) | Zhong, Ru-Gang (Zhong, Ru-Gang.) (Scholars:钟儒刚)

Indexed by:

Scopus SCIE

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)

Keyword:

Density functional calculations Electrochemistry Catechols Ketene N,N-acetals Green chemistry Arylation reaction Heterocycles

Author Community:

  • [ 1 ] [Zeng, Cheng-Chu]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 2 ] [Ping, Da-Wei]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 3 ] [Hu, Li-Ming]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 4 ] [Zhong, Ru-Gang]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China
  • [ 5 ] [Xu, Yi-Sheng]Chinese Res Inst Environm Sci, Atmospher Chem & Aerosol Res Dept, Beijing 100012, Peoples R China

Reprint Author's Address:

  • 曾程初

    [Zeng, Cheng-Chu]Beijing Univ Technol, Coll Life Sci & Bioengn, Beijing 100124, Peoples R China

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Source :

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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