Lillica
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Does ortholithiation work on non-tertiary anilines?
The only references I can readily find about ortholithiation of anilines seem to focus almost exclusively on tertiary anilines. Is it possible to do
such a reaction on a secondary aniline such as n-methylaniline, or would that free hydrogen group on the nitrogen pose an issue?
Edit: Using n-butyllithium
[Edited on 23-4-2017 by Lillica]
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clearly_not_atara
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It lithiates the nitrogen, so no.
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Lillica
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Figured that may happen. Do you know of a nitrogen/amine protecting group that is able to withstand Butyllithium so that I can pull off an
ortholithiation, followed by an alkylation, and then removal of the protecting group?
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CuReUS
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Quote: Originally posted by Lillica  | | Do you know of a nitrogen/amine protecting group that is able to withstand Butyllithium so that I can pull off an ortholithiation, followed by an
alkylation, and then removal of the protecting group? |
there is no need for any protecting group,since N-buLi is cheap and butane is a gas(so it will just fly out of the reaction rather than staying and
giving rise to side products).Just use a slight excess of 2 moles of n-buLi
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