This analysis explores lithiation mechanisms and compares them to traditional electrophilic substitution methods.
Functionalisation of a (hetero)aromatic ring by selectively (directedly) removing protons using the metal lithium is a relative mechanistic newcomer, compared to the pantheon of knowledge on aromatic electrophilic substitution. Investigating the mechanism using quantum calculations poses some interesting challenges, ones I have not previously discussed on this blog.
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Henry S. Rzepa (2013) studied this question.
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