Issue 15, 2018

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids


Methods for the conversion of aliphatic acids to alkyl halides have progressed significantly over the past century, however, the analogous decarboxylative bromination of aromatic acids has remained a longstanding challenge. The development of efficient methods for the synthesis of aryl bromides is of great importance as they are versatile reagents in synthesis and are present in many functional molecules. Herein we report a transition metal-free decarboxylative bromination of aromatic acids. The reaction is applicable to many electron-rich aromatic and heteroaromatic acids which have previously proved poor substrates for Hunsdiecker-type reactions. In addition, our preliminary mechanistic study suggests that radical intermediates are not involved in this reaction, which is in contrast to classical Hunsdiecker-type reactivity. Overall, the process demonstrates a useful method for producing valuable reagents from inexpensive and abundant starting materials.

Graphical abstract: Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

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Article information

Article type
Edge Article
02 Mar 2018
24 Mar 2018
First published
26 Mar 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 3860-3865

Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

Jacob M. Quibell, G. J. P. Perry, D. M. Cannas and I. Larrosa, Chem. Sci., 2018, 9, 3860 DOI: 10.1039/C8SC01016A

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