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Topic: Electrophillic addition to C3 on pyridine.  (Read 2412 times)

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Offline Nokovi

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Electrophillic addition to C3 on pyridine.
« on: January 03, 2015, 06:14:53 AM »
I've been searching through the literature for a while now and can't seem to find any reasonable processes for alkylating pyridine at the C3 position. My substrate will act as an electrophile (it's a tosylate/mesylate group) and pyridine should be a nucleophile but I'm not sure how to get the two to react. Most places either say nothing at all or that it's incredibly difficult. Please can someone help me? It'd be much appreciated!
Found a little bit of into about N-hydroxylated pyridine being better able to attack electrophiles, anyone done this before?

Offline phth

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Re: Electrophillic addition to C3 on pyridine.
« Reply #1 on: January 08, 2015, 11:21:30 AM »
It may be possible to turn it into a nucleophile first then turn that into an electrophile. 1) http://en.wikipedia.org/wiki/4-Dimethylaminopyridine. 2) Chem. Eur. J. 2012, 18, 3831 – 3834

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