A 1,2-regioselective reduction of α,β-unsaturated ketones to their corresponding allylic alcohols is accomplished with NaBH4 in the presence of acidic activated alumina rehydrated to the Brockmann II grade by adding 3 % w/w water. The substrate scope includes eight ketones reduced in high regio- and diastereoselectivity to their corresponding allylic alcohols. This is the first example of the strategy of systematically tuning the surface chemistry of alumina via partial rehydration in order to modulate selectivity in a reaction. Alumina is an appealing alternative to the common Luche reduction additive, CeCl3, from the perspective of cost and procedural simplicity.

A simple and inexpensive methodology is reported for the conversion of alkenes to 1,2-dibromo alkanes via oxidative bromination using HBr paired with dimethyl sulfoxide, which serves as the oxidant as well as cosolvent. The substrate scope includes 21 olefins brominated in good to excellent yields. Three of six styrene derivatives yielded bromohydrins under the reaction conditions.

A unique synthesis of aryl methyl sulfides is reported proceeding via reduction of dimethylsulfoxide to dimethylsulfide at elevated temperature in the presence of Hunig’s base followed by nucleophilic aromatic substitution and demethylation. Activated aryl fluorides, chlorides, and nitrobenzenes are suitable substrates with 13 examples provided. Dimethylsulfoxide serves as a simple and inexpensive formal source of the thiomethyl moiety.