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The use of carboxylic acids as traceless directing groups for regioselective C-H bond functionalisation

The use of carboxylic acids as traceless directing groups for regioselective C-H bond functionalisation
The use of carboxylic acids as traceless directing groups for regioselective C-H bond functionalisation

The ability to selectively functionalise a specific C-H bond is a long-standing challenge due to the ubiquity of such bonds in organic molecules. One of the most common approaches to overcome this obstacle consists of installing directing groups into substrates to direct the functionalisation towards the desired C-H bond, leaving behind the directing group in the molecule. Alternatively, carboxylic acids have been employed as traceless directing groups that are easily removed after carboxylic acid-directed installation of the desired functionality. This review focuses on the development of this concept and its application to organic synthesis during the last decade.

1359-7345
5584-5597
Font, Marc
0b95b0c8-232a-4018-867c-090e5567f592
Quibell, Jacob M.
353ce662-ff59-4f48-bcfc-ac01c3625ffb
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Larrosa, Igor
6ab25161-9d87-4f15-8559-0c0e59810989
Font, Marc
0b95b0c8-232a-4018-867c-090e5567f592
Quibell, Jacob M.
353ce662-ff59-4f48-bcfc-ac01c3625ffb
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Larrosa, Igor
6ab25161-9d87-4f15-8559-0c0e59810989

Font, Marc, Quibell, Jacob M., Perry, Gregory J.P. and Larrosa, Igor (2017) The use of carboxylic acids as traceless directing groups for regioselective C-H bond functionalisation. Chemical Communications, 53 (41), 5584-5597. (doi:10.1039/c7cc01755c).

Record type: Article

Abstract

The ability to selectively functionalise a specific C-H bond is a long-standing challenge due to the ubiquity of such bonds in organic molecules. One of the most common approaches to overcome this obstacle consists of installing directing groups into substrates to direct the functionalisation towards the desired C-H bond, leaving behind the directing group in the molecule. Alternatively, carboxylic acids have been employed as traceless directing groups that are easily removed after carboxylic acid-directed installation of the desired functionality. This review focuses on the development of this concept and its application to organic synthesis during the last decade.

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More information

Published date: 2017
Additional Information: Publisher Copyright: © 2017 The Royal Society of Chemistry.

Identifiers

Local EPrints ID: 475277
URI: http://eprints.soton.ac.uk/id/eprint/475277
ISSN: 1359-7345
PURE UUID: 12538a3e-488e-43cd-88f4-fdcd628af847
ORCID for Gregory J.P. Perry: ORCID iD orcid.org/0000-0001-8173-3369

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Date deposited: 14 Mar 2023 18:01
Last modified: 06 Jun 2024 02:17

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Contributors

Author: Marc Font
Author: Jacob M. Quibell
Author: Gregory J.P. Perry ORCID iD
Author: Igor Larrosa

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