Strategic installation of methyl groups within existing drugs or agrochemicals can lead to dramatic potency improvements via the Magic Methyl Effect (Scheme 1). Surprisingly, despite a recent “call for new C–H methylation reactions”, such protocols remain under-represented. Recently, aryl trimethylammonium salts have gained interest for use as synthetic methylating reagents due to their low volatility and toxicity. However, as these salts are also used in arylation chemistries, the mechanistic understanding of their reactivity is lacking (Scheme 2). This lecture details a full mechanistic study on the degradation properties of anilinium halides to bring these valuable salts under predictable synthetic control for methylation and arylation chemistries.

Anilinium salts in methylation reactions: An experimental and computational study

255th National Meeting (2018)

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