Regiospecific oxidation of polycyclic aromatic phenols to quinones by hypervalent iodine reagents

Autor:	Trevor M. Penning, Anhui Wu, Ronald G. Harvey, Daiwang Xu, Yazhen Duan
Rok vydání:	2010
Předmět:	chemistry.chemical_classification Organic Chemistry Iodobenzene Hypervalent molecule Regioselectivity Biochemistry Article Quinone chemistry.chemical_compound Hydrocarbon chemistry Reagent Drug Discovery Phenol Organic chemistry Phenols
Zdroj:	Tetrahedron. 66:2111-2118
ISSN:	0040-4020
Popis:	The hypervalent iodine reagents o-iodoxybenzoic acid (IBX) and bis(trifluoro-acetoxy)iodobenzene (BTI) are shown to be general reagents for regio-controlled oxidation of polycyclic aromatic phenols (PAPs) to specific isomers (ortho, para, or remote) of polycyclic aromatic quinones (PAQs). The oxidations of a series of PAPs with IBX take place under mild conditions to furnish the corresponding ortho-PAQs. In contrast, oxidations of the same series of PAPs with BTI exhibit variable regiospecificity, affording para-PAQs where structurally feasible and ortho-PAQs or remote PAQ isomers in other cases. The structures of the specific PAQ isomers formed are predictable on the basis of the inherent regioselectivities of the hypervalent iodine reagents in combination with the structural requirements of the phenol precursors. IBX and BTI are recommended as the preferred reagents for regio-controlled oxidation of PAPs to PAQs.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::0308121c438ba08c12f38936388df020 https://doi.org/10.1016/j.tet.2009.12.022 Zobrazit plný text záznamu Full Text from ScienceDirect