Introducing Sustainability into Industrial Homogeneous Catalysis

This thesis describes four projects focused on the implementation of green chemistry and engineering in an industrial context. The first project describes efforts to transition Meerwein-Ponndorf-Verley reduction technology from a batch-wise production framework to a continuous-flow framework. This work was done in the context of improving the synthesis of HIV-protease inhibitor intermediates. The second project describes a similar transfer of hydropyridoindole synthesis technology from batch processing to continuous-flow processing. In particular, a tandem synthetic pathway was developed for conducting cyclopropanation and ring-opening cyclization reactions in series. The third project describes the development of a novel catalyst separation process incorporating the use of sulfur-containing additives and Organic-Aqueous Tunable Solvents. Specifically, this process is demonstrated on palladium catalysts that have been employed in Suzuki coupling reaction mixtures. The fourth project describes the development of a recyclable catalytic system for use in Suzuki coupling reaction processes. The technology described incorporates the use of water-soluble ligands to generate hydrophilic palladium species that can be recovered via Organic-Aqueous Tunable Solvents and reintroduced as an active catalyst species.Ph.D