Oxidation of α-alkylbenzyl alcohols catalysed by 5,10,15,20- tetrakis(pentafluorophenyl)porphyrin iron(III) chloride. Competition between C-H and C-C bond cleavage

Article abstract of DOI:10.1016/S0040-4039(98)00863-6

The iodosylbenzene promoted oxidation of a number of α-alkylbenzyl alcohols catalysed by 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin iron(III) chloride (Fe(III)TPFPPCI) leads to the formation of C-H and C-C bond cleavage products, aryl ketones and benzaldehydes, respectively. It is suggested that the C-H bond cleavage path occurs through a hydrogen atom transfer (HAT) mechanism, whereas C-C bond cleavage products derive from the decomposition of an intermediate complex formed between the iron oxo complex and the alcohol.