Student Research

Bidentate N-Heterocyclic Carbene Nickel Complexes for Decarbonylation of Ketones

Achieving decarbonylation of ketones is of interest as a route towards synthesizing carbon-carbon bonds. However, decarbonylation requires the cleavage of two carbon-carbon bonds which are kinetically and thermodynamically more stable than the carbon-hydrogen bond of an aldehyde. A recent study first reported decarbonylation of ketones by nickel bound to phosphine or carbene ligands. This project aims to establish feasibility of using bidentate N-heterocyclic carbene (NHC) nickel complexes as catalysts for decarbonylation reactions. Three nickel complexes with varying ligand sterics were tested as catalysts in an initial reaction with benzophenone to establish feasibility. Following the reaction, the observation of biphenyl by GC-MS indicated that a decarbonylation had occurred. Future goals include tailoring the catalyst and reaction conditions to improve yields and expanding the scope to substituted ketones. Improving nickel mediated decarbonylation of ketones will be significant in the development of new reactions for synthesis of pharmaceuticals and fine chemicals.