Metal salt mediated radical reactions of 2-substituted-1, 4-naphthoquinones

Zhen Yu Lin, Yu Ling Chen, Chih Shone Lee, Che Ping Chuang

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

The silver(II)- and manganese(III)-mediated radical reactions of 2-substituted-l, 4-naphthoquinones are described. Acyl radicals generated by the oxidative decarboxylation of αketo acids with silver(I) nitrate and persulfate undergo efficient radical addition to the C=C bond of 2-(1-hydroxyalkyl)-1, 4-naphthoquinones and 2-(1-amidoalkyl)-1, 4naphthoquinones. This reaction provides an effective method for the synthesis of naphtho[2, 3-c]furan-4, 9-diones and benzo[f]isoindole-4, 9-diones. In the presence of O2, manganese(III) acetate oxidation of β-keto esters also generates acyl radicals, which then undergo radical addition to 2-(1-amidoalkyl)-1, 4-naphthoquinones, and subsequently, benzo[f]isoindole-4, 9-diones are produced.

Original languageEnglish
Pages (from-to)3876-3882
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number20
DOIs
Publication statusPublished - 2010 Jul 1

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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