Utilization of water as a solvent for catalyzed organic transformations relies on the formation of water soluble catalysts. The water soluble imidazolium salt 1,3-bis(N-methylpyridinium-2-ylmethyl)imidazolium triiodide was synthesized and utilized as a supporting ligand for the formation of water soluble M-NHC catalysts. The novel catalyst [1,3-bis(N-methylpyridinium-2-ylmethyl)imidazolin-2-ylidene]Pd(II)I3 was tested towards Suzuki-Miyaura coupling in mixed aqueous-organic solvents. Initial catalytic results suggest the catalyst is responsible for homocoupling of phenylboronic acid, while palladium nanoparticles are likely responsible for the excellent cross-coupling conversion observed.

Synthesis and catalytic activity of water soluble N-heterocyclic carbene complexes

251st National Meeting (2016)

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