Presentation Title

Decarbonylation of Ketones with Bidentate N-Heterocyclic Carbene Nickel Complexes

Faculty Mentor

Dr. Chantal Stieber

Start Date

18-11-2017 10:00 AM

End Date

18-11-2017 11:00 AM

Location

BSC-Ursa Minor 108

Session

Poster 1

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

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.

Summary of research results to be presented

The produced Biphenyl was below detection limit so further goals must done to increase the yield. Some future works should include implementing other ketones, utilizing different ligand sterics, and changing the experimental conditions.

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Nov 18th, 10:00 AM Nov 18th, 11:00 AM

Decarbonylation of Ketones with Bidentate N-Heterocyclic Carbene Nickel Complexes

BSC-Ursa Minor 108

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.