Fe(ClO4)3·×H2O-Catalyzed direct C-C bond forming reactions between secondary benzylic alcohols with different types of nucleophiles

A mild and efficient Fe(ClO4)3·×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 anti-coagulant 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.

Graphical abstractDownload full-size imageA mild and efficient Fe(ClO4)3·×H2O-catalyzed direct C-C coupling bond ling reactions of 1,3-dicarbonyl compounds, electron-rich heteroarenes and arenes, and 4-hydroxycoumarin with secondary benzylic alcohols have been described.