Silyl trifluoromethanesulfonate-activated para-methoxybenzyl methyl ether as an alkylating agent for thiols and aryl ketones

para-Methoxybenzyl methyl ether acts as an alkylating agent for thiols in the presence of trimethylsilyl trifluoromethanesulfonate and trialkylamine base in good yields (58–96%). Aryl ketones are alkylated under similar conditions, probably through an enol silane intermediate, also in high yields (67–95%). The active alkylating species is likely a p-methoxybenzyl cation.