A General and Efficient Iron-Catalyzed Benzylation of 1,3-Dicarbonyl Compounds

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 inexpensiv...

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Published inAdvanced synthesis & catalysis Vol. 349; no. 6; pp. 865 - 870
Main Authors Kischel, Jette, Mertins, Kristin, Michalik, Dirk, Zapf, Alexander, Beller, Matthias
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 02.04.2007
WILEY‐VCH Verlag
Wiley
Subjects
1,3‐dicarbonyl compounds
3-dicarbonyl compounds
anticoagulants
benzylation
Chemistry
Chemistry, Applied
Chemistry, Organic
CC coupling
iron catalysis
Physical Sciences
Science & Technology
C-C coupling
ACTIVE-METHYLENE-COMPOUNDS
ALKENES
HETEROARENES
ACID
benzylation
ARENES
anticoagulants
1,3-dicarbonyl compounds
iron catalysis
MICHAEL REACTIONS
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Summary: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.
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ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200600497