So I have a simple N-TIPS iodopyrrole and I'm trying to exchange a TIPS group for a benzenesulfonyl group in one pot. The first time I tried it I got the desired in 60% yield by deprotection with TBAF, then quenching with benzenesulfonyl chloride in the presence of Et3N. I don't think the Et3N was necessary since there is no source of HX and the nucleophile is N-. I can't find any literature on this type of conversion, but I'm thinking maybe I should use catalytic DMAP. The reaction was way slower than I expected, and I'm thinking the Bu4N+/pyrrole N- ion pair is pretty tightly associated and that may be why the reaction is so slow.