Selective Iron-Mediated C- and O-Addition of Phenolic Nucleophiles to a Cyclohexadiene Scaffold Using Renewable Precursors
Journal article, 2019

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.

Iron

Metal carbonyl

Renewable resources

Phenols

Green chemistry

Cyclohexadiene

Water

Author

Petter Dunås

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Andrew Paterson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

G. Kociok-Köhn

University of Bath

Simon E. Lewis

University of Bath

Nina Kann

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

ACS Sustainable Chemistry & Engineering

2168-0485 (eISSN)

Vol. 7 7 7155-7162

Subject Categories

Chemical Process Engineering

Biocatalysis and Enzyme Technology

Organic Chemistry

DOI

10.1021/acssuschemeng.9b00127

More information

Latest update

7/16/2020