Melamine is an inexpensive aminotriazine that can be used as a ligand for palladium in Suzuki-Miyaura cross-coupling reactions. The melamine-palladium complex is soluble and catalytically active in both water and the sustainable organic solvent ethyl lactate. These efforts contribute to the growing commitment to employ sustainable reaction media in organic synthesis. The melamine-palladium complex can also be cross-linked in situ by reaction with formaldehyde to form an insoluble polymeric catalyst that can be recovered after cross-coupling reactions. In the course of these investigations we have also uncovered an interesting mechanistic aspect regarding the role of the base in aqueous cross-coupling reactions. These findings will be presented along with the practical applications of the melamine-palladium complex in synthesis.

Melamine is a versatile ligand for Suzuki-Miyaura cross-coupling in both water and sustainable organic solvents

247th National Meeting (2014)

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