Efficient and Versatile (De)Hydrogenation Catalysts

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This is a continuing program of research in Goussev's group at Wilfrid Laurier University, devoted to catalytic hydrogenation of C=X bonds and acceptorless dehydrogenative coupling (ADC) reactions of alcohols. We develop 'green' catalytic methods for making several major types of organic compounds ubiquitous in the synthesis of agrochemicals, pharmaceuticals, flavors and fragrances, and specialty chemicals. The objectives of the proposed research include: 1) Synthesis of a series of 'cooperating' amino-sulfide ligands. 2) Synthesis of a series of bifunctional catalysts based on the above ligands and transition metals from Group 8 (Iron, Ruthenium, and Osmium). 3) Extensive testing of the new catalysts in reactions of acceptorless dehydrogenative coupling (ADC) of alcohols, hydrogenation of esters, imines, and related substrates with C=X bonds. The new catalysts will conform to several practical requirements of medium- and large-scale organic preparations in academic and industrial settings: a) ease of catalyst synthesis on 10 - 100 g and possibly larger scale, b) low cost, c) air-stability, d) activity at loadings <100 ppm, e) activity below 100 degrees C, preferably at 20 - 40 degrees C, and d) high functional group tolerance and selectivity. The proposed work builds upon the NSERC-funded research in Goussev's group that produced most efficient catalysts known today for converting alcohols into carbonyl compounds (e.g. ethanol into ethylacetate) and for reduction of esters to alcohols under hydrogen, without using hazardous aluminum hydride reagents. The proposed research is expected to give novel efficient and versatile catalysts that would allow conducting several academically and industrially important organic syntheses following the principles of green chemistry, i.e. energy-saving, using low catalyst loadings, possessing excellent atom-efficiency, and producing little or no chemical waste.