Transition-metal-free decarboxylative bromination of aromatic carboxylic acids
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.
3860-3865
Quibell, Jacob M.
353ce662-ff59-4f48-bcfc-ac01c3625ffb
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Cannas, Diego M.
53f56735-8365-4d3d-b017-8290a1101532
Larrosa, Igor
6ab25161-9d87-4f15-8559-0c0e59810989
2018
Quibell, Jacob M.
353ce662-ff59-4f48-bcfc-ac01c3625ffb
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Cannas, Diego M.
53f56735-8365-4d3d-b017-8290a1101532
Larrosa, Igor
6ab25161-9d87-4f15-8559-0c0e59810989
Quibell, Jacob M., Perry, Gregory J.P., Cannas, Diego M. and Larrosa, Igor
(2018)
Transition-metal-free decarboxylative bromination of aromatic carboxylic acids.
Chemical Science, 9 (15), .
(doi:10.1039/c8sc01016a).
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.
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Published date: 2018
Additional Information:
Funding Information:
We gratefully acknowledge the Engineering and Physical Sciences Research Council for funding (EP/L014017/2 and EP/ K039547/1). We thank Dr Ralph Adams (UoM) for the quantitative NMR experiments.
Publisher Copyright:
© The Royal Society of Chemistry 2018.
Identifiers
Local EPrints ID: 475281
URI: http://eprints.soton.ac.uk/id/eprint/475281
ISSN: 2041-6520
PURE UUID: 0ee71df3-d031-4d41-a5ca-aab69832b7f4
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Date deposited: 14 Mar 2023 18:01
Last modified: 18 Mar 2024 04:11
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Contributors
Author:
Jacob M. Quibell
Author:
Gregory J.P. Perry
Author:
Diego M. Cannas
Author:
Igor Larrosa
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