Sn-zeolite beta as a heterogeneous chemoselective catalyst for Baeyer–Villiger oxidations

Avelino Corma (), Laszlo T. Nemeth, Michael Renz and Susana Valencia
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Avelino Corma: Instituto de Tecnología Química, UPV-CSIC
Laszlo T. Nemeth: Universal Oil Products, UOP LLC
Michael Renz: Instituto de Tecnología Química, UPV-CSIC
Susana Valencia: Instituto de Tecnología Química, UPV-CSIC

Nature, 2001, vol. 412, issue 6845, 423-425

Abstract: Abstract The Baeyer–Villiger oxidation, first reported more than 100 years ago1, has evolved into a versatile reaction widely used2 to convert ketones—readily available building blocks in organic chemistry—into more complex and valuable esters and lactones. Catalytic versions of the Baeyer–Villiger oxidation are particularly attractive for practical applications, because catalytic transformations simplify processing conditions while minimizing reactant use as well as waste production. Further benefits are expected from replacing peracids, the traditionally used oxidant, by cheaper and less polluting hydrogen peroxide3. Dissolved platinum complexes4 and solid acids, such as zeolites5,6 or sulphonated resins7, efficiently activate ketone oxidation by hydrogen peroxide. But these catalysts lack sufficient selectivity for the desired product if the starting material contains functional groups other than the ketone group; they perform especially poorly in the presence of carbon–carbon double bonds. Here we show that upon incorporation of 1.6 weight per cent tin into its framework, zeolite beta acts as an efficient and stable heterogeneous catalyst for the Baeyer–Villiger oxidation of saturated as well as unsaturated ketones by hydrogen peroxide, with the desired lactones forming more than 98% of the reaction products. We ascribe this high selectivity to direct activation of the ketone group, whereas other catalysts first activate hydrogen peroxide, which can then interact with the ketone group as well as other functional groups.

Date: 2001
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DOI: 10.1038/35086546

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