Enzyme-like C–H Oxidation of Glucosides Promoted by Visible Light

To match nature's prowess at using enzymes to make desired motifs in a regioselective fashion, we explore the use of visible light for the selective oxidation of the hydroxyl group to afford the corresponding keto-saccharide. This highly admirable approach offers several advantages over the enzymatic approach in terms of yields and the scope of substrates. Herein, we report the development of a simple visible-light-promoted selective oxidation of unprotected glucosides that allows for inexpensive access to valuable keto-saccharide building blocks. The method is employed on a variety of different natural and artificial glucosides, is operationally simple and scalable, and can be used to access keto-saccharides rapidly and inexpensively.