Tuning the Reactivity of Peroxo Anhydrides for Aromatic C–H Bond Oxidation

Phenol moieties are key structural motifs in many areas of chemical research from polymers to pharmaceuticals. Herein, we report on the design and use of a structurally demanding cyclic peroxide (spiro­[bicyclo[2.2.1]­heptane-2,4′-[1,2]­dioxolane]-3′,5′-dione, P4) for the direct hydroxylation of aro...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-09, Vol.83 (17), p.10070-10079
Main Authors: Pilevar, Afsaneh, Hosseini, Abolfazl, Šekutor, Marina, Hausmann, Heike, Becker, Jonathan, Turke, Kevin, Schreiner, Peter R
Format: Article
Language:English
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Summary:Phenol moieties are key structural motifs in many areas of chemical research from polymers to pharmaceuticals. Herein, we report on the design and use of a structurally demanding cyclic peroxide (spiro­[bicyclo[2.2.1]­heptane-2,4′-[1,2]­dioxolane]-3′,5′-dione, P4) for the direct hydroxylation of aromatic substrates. The new peroxide benefits from high thermal stability and can be synthesized from readily available starting materials. The aromatic C–H oxidation using P4 exhibits generally good yields (up to 96%) and appreciable regioselectivities.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b01392