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A General and Efficient Iron‐Catalyzed Benzylation of 1,3‐Dicarbonyl Compounds
Author(s) -
Kischel Jette,
Mertins Kristin,
Michalik Dirk,
Zapf Alexander,
Beller Matthias
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600497
Subject(s) - chemistry , yield (engineering) , catalysis , phenprocoumon , iron(iii) chloride , organic chemistry , chloride , 4 hydroxycoumarin , reaction conditions , medicinal chemistry , combinatorial chemistry , warfarin , metallurgy , atrial fibrillation , medicine , materials science , cardiology
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)‐2 H ‐chromen‐2‐ones. As an example the anticoagulant Phenprocoumon is prepared in one step from commercially available substrates in 94 % yield.