Fe(ClO4)3•xH2O-Catalyzed direct C-C bond forming reactions between secondary benzylic alcohols with different types of nucleophiles

A mild and efficient Fe(ClO4)(3) center dot x H2O-catalyzed direct C-C bond coupling reactions of 1,3-dicarbonyl compounds, electron-rich arenes and heteroarenes and 4-hydroxycoumarin with secondary benzylic alcohols have been described. The benzylation of electron-rich arenes and heteroarenes leads to the synthesis of bis-symmetrical triarylmethanes. The present method is also applied to synthesis of an anticoagulant compound, 4-hydroxy-3-(1,2,3,4-tetrahydronaphthalen-1-yl)-2H-chromen-2-one (Coumatetralyl (B)) from commercially available substrates was obtained in 85% yield. The advantages of this protocol are broad scope, mild conditions, use of inexpensive catalyst and simplicity of operation since water is the only side product. (C) 2010 Elsevier Ltd. All rights reserved.