KF/alumina catalyzed regioselective benzylation and benzoylation using solvent-free grind-stone chemistry?

RSC Advances Pub Date: 2012-08-15 DOI: 10.1039/C2RA21154H

Abstract

Potassium fluoride-impregnated on alumina catalyzes solvent-free regioselective O-benzylation, benzoylation and cinnamylation of phenols. Reaction proceeds simply by triturating together equivalent amounts of phenol and corresponding halide in the presence of 5 mol% of KF/alumina for 5–20 min with a mortar and pestle, without need for any additive such as phase-transfer catalyst or solvent. Key features of the protocol include its efficiency also for solid–solid precursors and regioselectivity for phenolic hydroxyls versus alcoholic hydroxyls. Utility of the protocol for N- and S-benzylation has also been explored. Products were obtained in excellent yields and the catalyst can be easily recycled several times without significant loss of activity.

Graphical abstract: KF/alumina catalyzed regioselective benzylation and benzoylation using solvent-free grind-stone chemistry
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