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Photocatalytic Hydrogenolysis Of Allylic Alcohols For Rapid Access To Platform Chemicals And Fine Chemicals

Yuki Takada, Joaquim Caner, Hiroshi Naka, Susumu Saito

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AbstractA brief account of our recent work on the chemo-, regio- and stereoselective photocatalytic hydrogenolysis of allylic alcohols to alkenes promoted by palladium-loaded titanium oxide (Pd/TiO2) photocatalysts is presented. Since methanol is employed as the reducing agent, the method does not involve stoichiometric generation of salt waste. The photocatalytic hydrogenolysis proceeds at room temperature, and is compatible with the presence of functional groups such as C=C double bonds and hydroxyl groups at non-allylic positions. The regioselectivity is predictable: the hydrogen atom is predominantly incorporated into the sterically less hindered carbon atom of the allylic moiety. This protocol should provide straightforward green access to a range of platform chemicals (exemplified by the two-step synthesis of propylene from glycerol) and fine chemicals [e.g. (S)-(+)-lavandulol from (R)-(–)-carvone] without the need for protection/deprotection steps.