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

Petter Dunås, Andrew J. Paterson, Gabriele Kociok-Köhn, Simon E. Lewis, Nina Kann

Research output: Contribution to journalArticle

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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.

Original languageEnglish
Pages (from-to)7155-7162
Number of pages8
JournalACS Sustainable Chemistry and Engineering
Volume7
Issue number7
Early online date28 Feb 2019
DOIs
Publication statusPublished - 1 Apr 2019

Keywords

  • Cyclohexadiene
  • Green chemistry
  • Iron
  • Metal carbonyl
  • Phenols
  • Renewable resources
  • Water

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment

Cite this

Selective Iron-Mediated C- and O-Addition of Phenolic Nucleophiles to a Cyclohexadiene Scaffold Using Renewable Precursors. / Dunås, Petter; Paterson, Andrew J.; Kociok-Köhn, Gabriele; Lewis, Simon E.; Kann, Nina.

In: ACS Sustainable Chemistry and Engineering, Vol. 7, No. 7, 01.04.2019, p. 7155-7162.

Research output: Contribution to journalArticle

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