Light induced vanadium catalyzed aerobic oxidation of vicinal diols

The oxidative cleavage of carbon-carbon bond of vicinal diols to yield carbonyl compounds is a very important reaction in organic synthesis. In the general context of renewable feedstock transformation, like lignin and sugars, the development of more sustainable and efficient methods is an essential research goal.In this sense, aerobic photoinduced processes has attracted much attention because of its unique advantages: milder conditions, more selectivity and execution even at room temperature. In this contest, vanadium catalyzed reactions plays a major role.Here we present a new catalytic system based on an aminotriphenolate complex (V1), previously used under thermal condition,that promotes aerobic C-C bond oxidative cleavage of vicinal diols under visible light at room temperature in presence of molecular oxygen. The optimization of the reaction conditions and the scope of the reaction will be described with benzylic and aliphatic 1,2-diols affording the corresponding aldehydes in very high yields at room temperature. Mechanistic studies and implementations of our method in more complex substrates like lignin models are currently ongoing in our laboratories and will be reported in due course.