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ChemistryOpen. 2012 Dec;1(6):245-50. doi: 10.1002/open.201200037. Epub 2012 Nov 6.

Facile oxidative rearrangements using hypervalent iodine reagents.

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1
School of Chemistry, Cardiff University Park Place, Main Building, Cardiff CF10 3AT (United Kingdom) E-mail: wirth@cf.ac.uk.

Abstract

Aromatic substituents migrate in a novel oxidative cyclization mediated by iodine(III) reagents. 4-Arylbut-3-enoic acids are cyclized and rearranged to 4-arylfuran-2(5H)-ones by hypervalent iodine compounds in good to excellent yields under mild reaction conditions. Other ring sizes are also accessible. The mechanism of the reaction is described in detail, and calculations highlight the cationic nature of the intermediates in the rearrangement. The fast access to heavily substituted furanones is used for the synthesis of biologically active derivatives.

KEYWORDS:

calculations; cyclizations; hypervalent iodine; oxidations; rearrangements

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