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DOI: 10.1055/s-0037-1610717
Single-Step Dual Functionalization: One-Pot Bromination-Cross-Dehydrogenative Esterification of Hydroxy Benzaldehydes with CCl3Br – A Comparison with Selectfluor
Publication History
Received: 07 April 2019
Accepted after revision: 27 May 2019
Publication Date:
19 June 2019 (online)
![](https://www.thieme-connect.de/media/synlett/201914/lookinside/thumbnails/st-2019-k0198-l_10-1055_s-0037-1610717-1.jpg)
Dedicated to Professor Ganesh P. Pandey on the occasion of his 63rd birthday.
Abstract
Bromination of phenolic compounds without directly using molecular bromine possesses much importance. In this article an IrIII/CCl3Br-assisted single-step double functionalization of hydroxy benzaldehydes is reported. It involves simultaneous esterification of the aldehyde group and bromination of the aryl ring of phenolic aldehydes in one-pot. The reaction proceeds under mild conditions in the presence of 445 nm blue LED light to obtain highly functionalized bromo hydroxy benzoates in moderate to good yields. In comparison, Selectfluor as an oxidant gives only non-bromo phenolic esters.
Key words
photoredox catalysis - iridium - cross-dehydrogenative coupling - aldehydes - bromo hydroxy benzoates - SelectfluorSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610717.
- Supporting Information
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For reviews on visible light photoredox catalysis, see:
For the importance of esters, see:
For the syntheses of aldehyde to ester, see:
For the photocatalytic syntheses of aldehyde to ester, see: