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Topic: N-TIPC pyrrole to N-sulfonyl pyrrole one pot  (Read 1547 times)

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Offline 23SigmaTropic

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N-TIPC pyrrole to N-sulfonyl pyrrole one pot
« on: November 04, 2016, 09:53:03 AM »

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.


Offline kriggy

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Re: N-TIPC pyrrole to N-sulfonyl pyrrole one pot
« Reply #1 on: November 04, 2016, 10:16:20 AM »
And what exactly is your problem? 60% is not bad.

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