GENERAL METHODS: ReIO2(PPh3)2 (10 mol%) was dissolved in toluene (3 mL) and 4-methylsulfonylbenzonitrile (1 mmol) and PhSiH3 (300 mol%) were added sequentially. The reaction mixture was heated to reflux temperature and stirred under air atmosphere, and the reaction progress was monitored by TLC or 1H NMR. Upon completion of the reaction, the mixture was cooled to room temperature, activated carbon was added and stirred for 3 min, followed by filtration through an alumina/diatomaceous earth pad. An ether solution of HCl (1.5 mol) was added to the filtrate to induce precipitation of 4-(methylsulfonyl)benzylamine hydrochloride. The solid product was collected by filtration and washed with hexane to give pure 4-(methylsulfonyl)benzylamine hydrochloride, all of the products being known compounds.
