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Issue 24, 2009
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Preparation of phenolic compounds by decarboxylation of hydroxybenzoic acids or desulfonation of hydroxybenzenesulfonic acid, catalysed by electron rich palladium complexes

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Abstract

Phenolic compounds can be prepared by catalytic decarboxylation of 4-hydroxybenzoic acid or desulfonation of 4-hydorxybenzene sulfonic acid. Palladium complexes are shown to be highly active in the decarboxylation reaction, but complexes of platinum or ruthenium also show some activity in this reaction. Highly electron donating diphosphines such as BDTBPMB or monophosphines such as PtBu3 were found to be more effective than the less donating dppe or PPh3. The addition of D2O led to deuteration of the aromatic ring mainly in the position ortho to the hydroxyl group. Phenol can also be generated by SO3extrusion from 4-hydroxybenzenesulfonic acid catalysed by highly electron rich palladium complexes.

Graphical abstract: Preparation of phenolic compounds by decarboxylation of hydroxybenzoic acids or desulfonation of hydroxybenzenesulfonic acid, catalysed by electron rich palladium complexes

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Publication details

The article was received on 08 Jan 2009, accepted on 25 Mar 2009 and first published on 27 Apr 2009


Article type: Paper
DOI: 10.1039/B900398C
Citation: Dalton Trans., 2009,0, 4683-4688
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    Preparation of phenolic compounds by decarboxylation of hydroxybenzoic acids or desulfonation of hydroxybenzenesulfonic acid, catalysed by electron rich palladium complexes

    A. A. Núñez Magro, G. R. Eastham and D. J. Cole-Hamilton, Dalton Trans., 2009, 0, 4683
    DOI: 10.1039/B900398C

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