A direct deoxygenative alkylation of benzylic and unactivated alkyl alcohols was developed with sulfones as the alkylation reagent, the (PCN)IrHCl complex as the catalyst, and KOtBu as the additive. This protocol offers an efficient approach for the direct conversion of hydroxy groups to alkyl groups without the need for an extra hydrogen source. The utility of this reaction was demonstrated by gram-scale synthesis and derivatization of a bioactive molecule.