Chlorotrimethylsilane and Sodium Iodide: A Useful Combination for the Regioselective Deoxygenation of Arylalkyl‐α‐Diketones

Abstract An efficient regioselective deoxygenation of arylalkyl‐1,2‐diketones by the couple trimethylsilylchloride/sodium iodide has been reported. In all cases, the deoxygenation takes place on the carbonyl group (Cα=O) proximal to the aromatic ring in methylene chloride at room temperature in good yields, furnishing a series of variously functionalized alkylbenzylketones. A large range of functional groups were well tolerated on the ortho‐ , meta‐ and para ‐positions by this mild process regardless of their electronic effects, demonstrating the general character of the present methodology. The trimethylsilylchloride/sodium iodide reducing process was also successfully applied to reduce α‐ketoacid and α‐ketoester substrates. magnified image