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Selective Iron-Mediated C- and O-Addition of Phenolic Nucleophiles to a Cyclohexadiene Scaffold Using Renewable Precursors

OAI: oai:purehost.bath.ac.uk:publications/07ffc182-8e3c-430e-b276-688ce1ccea5d • DOI: https://doi.org/10.1021/acssuschemeng.9b00127
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Abstract

Renewable phenols have been investigated as nucleophiles for the addition to a cationic cyclohexadienyl iron carbonyl scaffold. Benign conditions compatible with solvents such as ethanol and water were developed, and for the first time, selective C- or O-addition could be achieved. In addition, a novel atom-economic approach to forming the C-addition products directly from the neutral precursor complex in a single step using a catalytic acid is described. The formed C-addition product could then be selectively demetalated to form one of two different product classes, a functionalized arene or a cyclohexadiene.