Oxidation of caffeine with hydrogen peroxide catalyzed by metalloporphyrins
authors Neves, CMB; Simoes, MMQ; Santos, ICMS; Domingues, FMJ; Neves, MGPMS; Paz, FAA; Silva, AMS; Cavaleiro, JAS
nationality International
journal TETRAHEDRON LETTERS
author keywords Caffeine; Biomimetic oxidation; Manganese porphyrins; Hydrogen peroxide
keywords EPOXIDATION REACTIONS; PORPHYRIN COMPLEXES; MN(III) PORPHYRINS; MASS-SPECTROMETRY; METABOLISM; HISTORY
abstract The biomimetic oxidation of caffeine with hydrogen peroxide using metalloporphyrins as catalysts, which are known to be good biomimetic models of cytochrome P450 enzymes, is investigated. The two manganese porphyrins tested, chloro[5,10,15,20-tetrakis(2,6-dichlorophenyl)porphyrinato]manganese(III), [Mn(TDCPP)Cl], and chloro [5,10,15,20-tetrakis(pentafluorophenyl)porphyrinato]manganese(III), [Mn(TPEPP)Cl], afford high conversions of caffeine for all substrate/catalyst molar ratios. Selectivity was found to be dependent on the catalyst employed, and a new spiro racemic compound is described and fully characterized in the solid state from X-ray diffraction studies. (C) 2011 Elsevier Ltd. All rights reserved.
publisher PERGAMON-ELSEVIER SCIENCE LTD
issn 0040-4039
year published 2011
volume 52
issue 22
beginning page 2898
ending page 2902
digital object identifier (doi) 10.1016/j.tetlet.2011.03.139
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000291072300025
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journal impact factor 2.275
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