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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: 23SigmaTropic on November 04, 2016, 09:53:03 AM

Title: N-TIPC pyrrole to N-sulfonyl pyrrole one pot
Post by: 23SigmaTropic on November 04, 2016, 09:53:03 AM

Hello,

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.

Thanks!

Title: Re: N-TIPC pyrrole to N-sulfonyl pyrrole one pot
Post by: kriggy on November 04, 2016, 10:16:20 AM

And what exactly is your problem? 60% is not bad.