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