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]clearly_not_atara - 22-4-2017 at 23:13
It lithiates the nitrogen, so no.Lillica - 22-4-2017 at 23:31
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?CuReUS - 23-4-2017 at 00:09
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
