Oxidation of α,β-Unsaturated Ketones by Organophotocatalysis Using Rhodamine 6G under Visible Light Irradiation: Insight into the Reaction Mechanism

Author:

Yoshioka Eito,Takahashi Hiroki,Miyabe Hideto,Wanibe Hikari,Hontani Yukina,Hatsuse Kouki,Shimizu Remi,Kawashima Akira,Kohtani Shigeru

Abstract

AbstractThe oxidative transformation of α,β-unsaturated ketones was investigated under visible-light-induced photocatalytic conditions using rhodamine 6G as an organophotocatalyst. In this organocatalysis, the mild co-oxidant bromotrichloromethane (BrCCl3) acts not only as a quencher toward the activated photocatalyst species, having reductant properties, but also as a brominating reagent for the intermediate radicals. This study shows that bromine atom transfer from BrCCl3 to intermediate radicals is a key step in the reaction mechanism of our oxidation method.

Funder

Japan Society for the Promotion of Science

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

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