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Physical Sciences and Mathematics Commons

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Chemistry

University of Arkansas, Fayetteville

Theses/Dissertations

2011

Pure sciences; Asymmetric catalysis; Copper carbenoid; Enantioselective hydrosilylation; Heterocyclic carbenes

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Full-Text Articles in Physical Sciences and Mathematics

The Design, Synthesis And Application Of A Novel Class Of N-Heterocyclic Carbene Catalysts, Abigail Lynn Hubbard Dec 2011

The Design, Synthesis And Application Of A Novel Class Of N-Heterocyclic Carbene Catalysts, Abigail Lynn Hubbard

Graduate Theses and Dissertations

A copper carbenoid representative of a novel class of N-heterocyclic carbene (NHC) catalysts has been synthesized. This compound was characterized by X-ray crystallography and was found to confirm the rationale of our synthetic design: The C2-symmetric structure places four stereocenters in close proximity (<5Å) to the reactive site of the carbene via a trans-annular gearing effect. The copper carbenoid was found to catalyze the hydrosilylation of prochiral ketones with superb selectivity in high yield.