Facile Synthesis of Halogen Decorated para-/meta-Hydroxy­benzoates by Iridium-Catalyzed Borylation and Oxidation

Tayyaba Shahzadi; Rahman S. Z. Saleem; Ghayoor A. Chotana

doi:10.1055/s-0037-1610538

Synthesis, Table of Contents

Synthesis 2018; 50(21): 4336-4342
DOI: 10.1055/s-0037-1610538

paper

Facile Synthesis of Halogen Decorated para-/meta-Hydroxybenzoates by Iridium-Catalyzed Borylation and Oxidation

Authors

Tayyaba Shahzadi

Department of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan Email: ghayoor.abbas@lums.edu.pk
Rahman S. Z. Saleem

Department of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan Email: ghayoor.abbas@lums.edu.pk
Ghayoor A. Chotana*

Department of Chemistry & Chemical Engineering, Syed Babar Ali School of Science & Engineering, Lahore University of Management Sciences, Lahore 54792, Pakistan Email: ghayoor.abbas@lums.edu.pk

Abstract

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Abstract

Hydroxybenzoates are an important class of phenols that are widely used as preservatives and antiseptics in the food and pharmaceutical industries. In this report, a facile preparation of 2,6- and 2,3-disubstituted 4/5-hydroxybenzoates by iridium-catalyzed borylation of respective disubstituted benzoate esters followed by oxidation is described. This synthetic route allows for the incorporation of halogens in the final hydroxybenzoates with substitution patterns not readily accessible by the traditional routes of aromatic functionalization.

Key words

iridium-catalyzed C–H borylation - oxidation - Oxone^® - hydroxybenzoates - parabens - preservatives - halogen - trifluoromethyl

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References

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Supplementary Material

Supporting Information (PDF)

Facile Synthesis of Halogen Decorated para-/meta-Hydroxy­benzoates by Iridium-Catalyzed Borylation and Oxidation

Authors

Facile Synthesis of Halogen Decorated para-/meta-Hydroxybenzoates by Iridium-Catalyzed Borylation and Oxidation