Carboxylic acid salts as dual-function reagents for Carboxylation and Carbon Isotope labeling
Carboxylic acid salts as dual-function reagents for Carboxylation and Carbon Isotope labeling
The potassium salts of carboxylic acids are developed as efficient carboxylating agents through CO2 exchange. We describe these carboxylates as dual-function reagents because they function as a combined source of CO2 and base/metalating agent. By using the salt of a commercially available carboxylic acid, this protocol overcomes difficulties when using CO2 gas or organometallic reagents, such as pressurized containers or strictly inert conditions. The reaction proceeds under mild conditions, does not require transition metals or other additives, and shows broad substrate scope. Through the preparation of several biologically important molecules, we show how this strategy provides an opportunity for isotope labeling with low equivalents of labeled CO2.
Carboxylation, Decarboxylation, Dual-Function Reagent, Isotope Labeling, Metalation
Wang, Shuo
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Larrosa, Igor
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Yorimitsu, Hideki
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Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
27 March 2023
Wang, Shuo
ab3ecb29-8245-4db3-9b4d-2c3949be5848
Larrosa, Igor
6ab25161-9d87-4f15-8559-0c0e59810989
Yorimitsu, Hideki
a2c027b0-9559-4027-be32-39e601818a88
Perry, Gregory J.P.
766e7fc8-abf3-4d1e-9949-c1b3439a2185
Wang, Shuo, Larrosa, Igor, Yorimitsu, Hideki and Perry, Gregory J.P.
(2023)
Carboxylic acid salts as dual-function reagents for Carboxylation and Carbon Isotope labeling.
Angewandte Chemie - International Edition, 62 (14), [e202218371].
(doi:10.1002/anie.202218371).
Abstract
The potassium salts of carboxylic acids are developed as efficient carboxylating agents through CO2 exchange. We describe these carboxylates as dual-function reagents because they function as a combined source of CO2 and base/metalating agent. By using the salt of a commercially available carboxylic acid, this protocol overcomes difficulties when using CO2 gas or organometallic reagents, such as pressurized containers or strictly inert conditions. The reaction proceeds under mild conditions, does not require transition metals or other additives, and shows broad substrate scope. Through the preparation of several biologically important molecules, we show how this strategy provides an opportunity for isotope labeling with low equivalents of labeled CO2.
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Angew Chem Int Ed - 2023 - Wang - Carboxylic Acid Salts as Dual‐Function Reagents for Carboxylation and Carbon Isotope
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Accepted/In Press date: 6 February 2023
e-pub ahead of print date: 26 February 2023
Published date: 27 March 2023
Additional Information:
Funding Information:
This work was supported by JSPS KAKENHI Grant No. JP19H00895, JST CREST Grant No. JPMJCR19R4 and Royal Society International Exchange Grant No. IEC\R3\213047. G.J.P.P. is the recipient of a JSPS Postdoctoral Fellowship for Research in Japan (KAKENHI Grant No. JP21F21039).
Publisher Copyright:
© 2023 Wiley-VCH GmbH.
Keywords:
Carboxylation, Decarboxylation, Dual-Function Reagent, Isotope Labeling, Metalation
Identifiers
Local EPrints ID: 476600
URI: http://eprints.soton.ac.uk/id/eprint/476600
ISSN: 1433-7851
PURE UUID: 4092233b-6478-43a6-9afa-7e2639870855
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Date deposited: 09 May 2023 17:09
Last modified: 17 Mar 2024 07:43
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Contributors
Author:
Shuo Wang
Author:
Igor Larrosa
Author:
Hideki Yorimitsu
Author:
Gregory J.P. Perry
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