Issue 7, 2011
From the journal:

RSC Advances

Novel biomimetic oxidation of lapachol with H2O2 catalysed by a manganese(iii) porphyrin complex

Sónia M. G. Pires,a   Rodrigo De Paula,†a   Mário M. Q. Simões,a   Artur M. S. Silva,a   M. Rosário M. Domingues,a   Isabel C. M. S. Santos,a   Maria D. Vargas,b   Vítor F. Ferreira,b   M. Graça P. M. S. Neves*a  and  José A. S. Cavaleiro*a  

* Corresponding authors

a Department of Chemistry and QOPNA, University of Aveiro, University Campus, Aveiro, Portugal
E-mail: gneves@ua.pt, jcavaleiro@ua.pt
Fax: +351234370084
Tel: +351234370710

b Chemistry Institute, Fluminense Federal University, Campus do Valonguinho, Niterói, RJ 24020-150, Brazil

Abstract

The biomimetic oxidation of lapachol (1) using aqueous hydrogen peroxide as oxidant and chloro[5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinatomanganese(III)] (Mn-Porph) as catalyst is described. A comparison between the obtained results and those described for the oxidation of lapachol using meta-chloroperoxybenzoic acid (m-CPBA) reveals, besides different reaction products, a completely different selectivity. Unlike the m-CPBA approach, where ortho-naphthoquinones are obtained, para-naphthoquinones are highly favoured when using Mn-Porph and H2O2. Moreover, a new lactone is isolated and characterized in the present work.

Graphical abstract: Novel biomimetic oxidation of lapachol with H2O2 catalysed by a manganese(iii) porphyrin complex

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Article information

DOI
https://doi.org/10.1039/C1RA00578B
Article type
Communication
Submitted
10 Aug 2011
Accepted
12 Aug 2011
First published
23 Sep 2011

RSC Adv., 2011,1, 1195-1199

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Novel biomimetic oxidation of lapachol with H2O2 catalysed by a manganese(III) porphyrin complex

S. M. G. Pires, R. D. Paula, M. M. Q. Simões, A. M. S. Silva, M. R. M. Domingues, I. C. M. S. Santos, M. D. Vargas, V. F. Ferreira, M. G. P. M. S. Neves and J. A. S. Cavaleiro, RSC Adv., 2011, 1, 1195 DOI: 10.1039/C1RA00578B

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