Volume 2, Issue 10 p. 1296-1302
Full Paper

Green Catalytic Baeyer–Villiger Oxidation with Hydrogen Peroxide in Water Mediated by PtII Catalysts

Alessandra Cavarzan

Alessandra Cavarzan

Dipartimento di Chimica, Università Ca' Foscari di Venezia, Dorsoduro 2137, 30123 Venezia (Italy), Fax: (+399) 041-2348517

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Dr. Alessandro Scarso

Dr. Alessandro Scarso

Dipartimento di Chimica, Università Ca' Foscari di Venezia, Dorsoduro 2137, 30123 Venezia (Italy), Fax: (+399) 041-2348517

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Dr. Paolo Sgarbossa

Dr. Paolo Sgarbossa

Dipartimento di Processi Chimici dell'Ingegneria, Università di Padova, Via F. Marzolo 9, 35131 Padova (Italy)

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Prof. Rino A. Michelin

Prof. Rino A. Michelin

Dipartimento di Processi Chimici dell'Ingegneria, Università di Padova, Via F. Marzolo 9, 35131 Padova (Italy)

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Prof. Giorgio Strukul

Prof. Giorgio Strukul

Dipartimento di Chimica, Università Ca' Foscari di Venezia, Dorsoduro 2137, 30123 Venezia (Italy), Fax: (+399) 041-2348517

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First published: 21 July 2010
Citations: 20

Graphical Abstract

BV wonder: Baeyer–Villiger oxidation of cyclic ketones with 35 % hydrogen peroxide as a green oxidant mediated by monomeric PtII complexes bearing alkyl diphosphines greatly benefits from the employment of water with anionic surfactants. Under such conditions, the reaction shows enhanced catalytic activity compared to that with organic solvents.

Abstract

Baeyer–Villiger oxidation of cyclic ketones with 35 % hydrogen peroxide as a green oxidant mediated by monomeric PtII complexes bearing alkyl diphosphines greatly benefits from the employment of water with anionic surfactants as reaction medium. Under such conditions, the reaction shows enhanced catalytic activity compared to that with organic solvents. For more acid sensitive substrates, hydrolysis of the lactone product to the corresponding hydroxy acid occurs. Mild experimental conditions, such as moderate temperature and low catalyst loading (≤2 % mol), enabled moderate to good yields.