Alcohol oxidation is a transformation of fundamental importance, but common approaches suffer from safety and/or environmental issues. For example, when strong oxidants are combined with organic compounds and solvents, runaway reactions are possible. These concerns grow as reactions are scaled up. Transfer dehydrogenations offer an attractive alternative because strong oxidants are not required; instead, a carbonyl compound serves as the terminal oxidant. (Cyclopentadienone)iron carbonyl compounds have been used as catalysts in the transfer dehydrogenation of alcohols using acetone as both the solvent and hydrogen acceptor, but acetone’s low oxidation potential creates a disfavored equilibrium when attempts are made to oxidize some secondary alcohols and a majority of primary alcohols. We aim to expand the scope of alcohols that can be oxidized by discovering a hydrogen acceptor with a higher oxidation potential that is compatible with this catalyst system. Ideally, the hydrogen acceptor will be derived from a renewable resource, which would lead to the development of a sustainable method for dehydrogenating alcohols. Our initial results describing the application of a biomass-derived aldehyde as a hydrogen acceptor will be discussed.

Exploration of hydrogen acceptors in (cyclopentadienone)iron carbonyl-catalyzed transfer dehydrogenations

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.