A general and efficient iron-catalyzed benzylation of 1,3-dicarbonyl compounds

Jette Kischel, Kristin Mertins, Dirk Michalik, Alexander Zapf, Matthias Beller

Research output: Contribution to journalArticlepeer-review

143 Scopus citations

Abstract

Various CH-acidic 1,3-dicarbonyl compounds and methyl 3-acetamidobut-2- enoate react with benzylic alcohols to give the corresponding 2-benzylated products in good to excellent yield. Typically, reactions proceed under mild conditions (50-80°C; air) in the presence of catalytic amounts of inexpensive iron chloride hexahydrate. The benzylation of 4-hydroxycoumarin gives the pharmaceutically interesting 4-hydroxy-3-(1-phenylethyl)-2H-chromen-2- ones. As an example the anticoagulant Phenprocoumon is prepared in one step from commercially available substrates in 94 % yield.

Original languageEnglish
Pages (from-to)865-870
Number of pages6
JournalAdvanced Synthesis and Catalysis
Volume349
Issue number6
DOIs
StatePublished - Apr 2007
Externally publishedYes

Keywords

  • 1,3-dicarbonyl compounds
  • Anticoagulants
  • Benzylation
  • C-C coupling
  • Iron catalysis

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