Atom Economical Photocatalytic Oxidation of Phenols and Site-Selective Epoxidation Toward Epoxyquinols

Atom Economical Photocatalytic Oxidation of Phenols and Site-Selective Epoxidation Toward Epoxyquinols

The discovery of a multiple-bond-forming process merging the singlet oxygen-mediated dearomatization of 3,4-disubstitued phenols and diastereo- and regioselective epoxidation is described. This one-pot strategy using a transition metal-free multicatalytic system comprised of rose bengal and cesium c...

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Bibliographic Details
Published in:Journal of organic chemistry Vol. 86; no. 24; pp. 18192 - 18203
Main Authors: Péault, Louis, Planchat, Aurélien, Nun, Pierrick, Le Grognec, Erwan, Coeffard, Vincent
Format: Journal Article
Language:English
Published: United States American Chemical Society 17-12-2021
Subjects:
Catalysis
Chemical Sciences
Organic chemistry
Oxidation-Reduction
Phenols
Rose Bengal
Singlet Oxygen
Transition Elements
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Summary:The discovery of a multiple-bond-forming process merging the singlet oxygen-mediated dearomatization of 3,4-disubstitued phenols and diastereo- and regioselective epoxidation is described. This one-pot strategy using a transition metal-free multicatalytic system comprised of rose bengal and cesium carbonate allowed the efficient formation of functionalized epoxyquinol products under mild conditions. Mechanistic investigations have been performed to shed the light on the key species involved in this transformation.
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02459