Methyl groups can imbue valuable
properties in organic molecules,
often leading to enhanced bioactivity. To enable efficient installation
of methyl groups on simple building blocks and in late-stage functionalization,
a nickel-catalyzed reductive coupling of secondary Katritzky alkylpyridinium
salts with methyl iodide was developed. When coupled with formation
of the pyridinium salt from an alkyl amine, this method allows amino
groups to be readily transformed to methyl groups with broad functional
group and heterocycle tolerance.
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