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Issue 15, 2018
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Transition-metal-free decarboxylative bromination of aromatic carboxylic acids

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Abstract

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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Publication details

The article was received on 02 Mar 2018, accepted on 24 Mar 2018 and first published on 26 Mar 2018


Article type: Edge Article
DOI: 10.1039/C8SC01016A
Citation: Chem. Sci., 2018,9, 3860-3865
  • Open access: Creative Commons BY license
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    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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