A review. Catecholic motifs are present in numerous natural products and synthetic compds. used in various sectors of the chem. industries such as food, cosmetic, pharmaceutical and polymer industries. The antioxidant activity usually conferred to compds. bearing catecholic motifs is the property on which their application is often based. Although several (bio) chem. methods are available to chemists to produce catechols, the oxygenation of phenols constitutes one of the most practical approaches as long as the o-selectivity of the process can be controlled. In this context, oxygenating hypervalent iodine(V) reagents offer a convenient metal-free soln. Among these reagents, 2-iodoxybenzoic acid (IBX) or its stabilized (non explosive) SIBX and polymer-supported versions have found the most useful and successful applications in the conversion of phenols into o-quinones, followed by redn. into catechols. Examples of oxygenative demethylation of 2-methoxyphenols and o-hydroxylation of phenolic compds. for the synthesis of biol. and industrially-relevant catechols are highlighted in this review article, together with some mechanistic discussions on these transformations.
Synthesis of biologically active catecholic compounds via ortho-selective oxygenation of phenolic compounds using hypervalent iodine(V) reagents / R., Bernini; Fabrizi, Giancarlo; L., Pouysegu; D., Deffieux; S., Quideau. - In: CURRENT ORGANIC SYNTHESIS. - ISSN 1570-1794. - STAMPA. - 9:(2012), pp. 650-669. [10.2174/157017912803251792]
Synthesis of biologically active catecholic compounds via ortho-selective oxygenation of phenolic compounds using hypervalent iodine(V) reagents
FABRIZI, Giancarlo;
2012
Abstract
A review. Catecholic motifs are present in numerous natural products and synthetic compds. used in various sectors of the chem. industries such as food, cosmetic, pharmaceutical and polymer industries. The antioxidant activity usually conferred to compds. bearing catecholic motifs is the property on which their application is often based. Although several (bio) chem. methods are available to chemists to produce catechols, the oxygenation of phenols constitutes one of the most practical approaches as long as the o-selectivity of the process can be controlled. In this context, oxygenating hypervalent iodine(V) reagents offer a convenient metal-free soln. Among these reagents, 2-iodoxybenzoic acid (IBX) or its stabilized (non explosive) SIBX and polymer-supported versions have found the most useful and successful applications in the conversion of phenols into o-quinones, followed by redn. into catechols. Examples of oxygenative demethylation of 2-methoxyphenols and o-hydroxylation of phenolic compds. for the synthesis of biol. and industrially-relevant catechols are highlighted in this review article, together with some mechanistic discussions on these transformations.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
