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Synthesis 2018; 50(21): 4336-4342
DOI: 10.1055/s-0037-1610538
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© Georg Thieme Verlag Stuttgart · New York

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

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
› Author AffiliationsWe thank Lahore University of Management Sciences for providing generous financial support for this research through start-up grant and faculty initiative fund to G.A.C. We also thank Higher Education Commission (HEC) of Pakistan for financial support through grant number NRPU-4426. T.S. is thankful to Lahore University of Management Sciences for a Ph.D. fellowship.
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Publication History

Received: 10 May 2018

Accepted after revision: 04 July 2018

Publication Date:
09 August 2018 (online)

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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610538.
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