Rhodium-catalyzed hydroacylation is a powerful and atom-economical method for synthesizing ketones from aldehydes and olefins. Despite this, a narrow scope of reactive substrates has limited the utility and broad application of this transformation. Efforts towards the development of new classes of reactive substrates have focused on the use of oxygen- and sulfur-containing olefins, which have enabled various modes of reactivity and thus allowed access to novel types of hydroacylation products. In addition to reactivity, a key to the success of these transformations is the control of regio-, stereo-, and chemoselectivity. In combination with substrate structure, strategies in enantioselective catalysis and metal-organic cooperative catalysis have been applied to achieve requisite reactivity and selectivity when required. A variety of products, such as medium-sized heterocycles, branched sulfur-containing and β-hydroxy ketones, and ketones bearing quaternary carbon centres have been synthesized via hydroacylation using these strategies. A method for preparing polyelectrolyte-stabilized palladium nanoparticles and their use in Suzuki coupling reactions have also been developed.
| Identifer | oai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/31725 |
| Date | 05 January 2012 |
| Creators | Coulter, Matthew |
| Contributors | Dong, Vy Maria |
| Source Sets | University of Toronto |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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