Publication: Direct decarboxylation of trifluoroacetates enabled by iron photocatalysis
Authors
Fernández-García, Sara ; Chantzakou, Veronika Olga ; Juliá Hernández, Francisco
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Publisher
Wiley, Gesellschaft Deutscher Chemiker
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DOI
https://doi.org/10.1002/anie.202311984
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info:eu-repo/semantics/article
Description
© 2023 The Authors. This manuscript version is made available under the CC-BY-NC 4.0 license http://creativecommons.org/licenses/by-nc/4.0/. This document is the Published version of a Published Work that appeared in final form in Angewandte Chemie International Edition. To access the final edited and published work see https://doi.org/10.1002/anie.202311984
Abstract
Trifluoroacetates are the most abundant and accessible sources of trifluoromethyl groups, which are key components in pharmaceuticals and agrochemicals. The generation of trifluoromethyl reactive radicals from
trifluoroacetates requires their decarboxylation, which is hampered by their high oxidation potential. This constitutes a major challenge for redox-based methods, because of the need to pair the redox potentials with trifluoroacetate. Here we report a strategy based on iron photocatalysis to promote the direct photodecarboxyla tion of trifluoroacetates that displays reactivity features that escape from redox limitations. Our synthetic design
has enabled the use of trifluoroacetates for the trifluoromethylation of more easily oxidizable organic substrates, offering new opportunities for late-stage derivatization campaigns using chemical feedstocks, Earth-abundant catalysts, and visible-light.
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Citation
Angew. Chem. Int. Ed. 2024, 63, e202311984
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