Amines bound to aromatic rings represent a common motif found in many of today’s drugs. Solution-based cross-coupling reactions of amines with aromatic halides can present significant purification difficulties. In addition to simplifying purification, performing these cross coupling reactions on solid support may help increase the efficiency of parallel syntheses and speed drug discovery efforts by making it easier to create libraries of lead and optimized drug candidates. Although amination of resin-bound aryl halides has been well studied, we explored the less well-known amination of aryl halides using resin-bound amines. Changes in solvent, base, catalyst, and ligand were first explored to discover ideal conditions for the amines being tested. The determined optimal conditions were then tested against a variety of both electron-rich and electron-deficient aryl halides to determine the scope of application for these solid-phase Buchwald-Hartwig reactions.

Buchwald-Hartwig amination of aryl halides using solid-phase primary and secondary amines

255th National Meeting (2018)

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