Organocatalytic Dakin oxidation by nucleophilic flavin catalysts

Organic Letters
Shuai ChenFrank W Foss

Abstract

Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.

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Citations

May 4, 2017·The Journal of Organic Chemistry·David TejedorFernando García-Tellado
Jun 17, 2015·Organic & Biomolecular Chemistry·H IidaS-I Murahashi
Mar 24, 2016·Organic & Biomolecular Chemistry·Alexander T MurrayDavid R Carbery
May 17, 2018·Organic & Biomolecular Chemistry·Takuya SakaiHiroki Iida
Jun 25, 2014·Physical Chemistry Chemical Physics : PCCP·Aleksandr V MarenichDonald G Truhlar
Aug 26, 2016·Beilstein Journal of Organic Chemistry·Ivan A YaremenkoAlexander O Terent'ev
Jul 25, 2014·Chemical Communications : Chem Comm·Shun-Ichi MurahashiKanji Meguro
Jun 20, 2015·Angewandte Chemie·Alexander T MurrayDavid R Carbery
Apr 27, 2017·Chemical Communications : Chem Comm·Wei LiWujiong Xia
Sep 8, 2018·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jan RichtarJozef Krajcovic
Jun 1, 2016·Chemistry : a European Journal·Attila KormányosKrishnan Rajeshwar
Jul 13, 2012·Organic Letters·Alexander T MurrayDavid R Carbery
Aug 17, 2012·Journal of the American Chemical Society·Hiroki IidaEiji Yashima
Oct 1, 2021·Science·Lu ChengWei Han

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