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

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 no...

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Bibliographic Details
Published inACS sustainable chemistry & engineering Vol. 7; no. 7; pp. 7155 - 7162
Main Authors Dunås, Petter, Paterson, Andrew J, Kociok-Köhn, Gabriele, Lewis, Simon E, Kann, Nina
Format Journal Article
LanguageEnglish
Published American Chemical Society 01.04.2019
Subjects
Cyclohexadiene
Green chemistry
Iron
Metal carbonyl
Phenols
Renewable resources
Water
Metal carbonyl
Water
Phenols
Cyclohexadiene
Iron
Green chemistry
Renewable resources
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Summary: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.
ISSN:2168-0485
2168-0485
DOI:10.1021/acssuschemeng.9b00127