Taking electrodecarboxylative etherification beyond Hofer–Moest using a radical C–O coupling strategy

Ángel Manu Martínez, Davit Hayrapetyan, Tim van Lingen, Marco Dyga and Lukas J. Gooßen ()
Additional contact information
Ángel Manu Martínez: Ruhr-Universität Bochum
Davit Hayrapetyan: Ruhr-Universität Bochum
Tim van Lingen: Ruhr-Universität Bochum
Marco Dyga: Ruhr-Universität Bochum
Lukas J. Gooßen: Ruhr-Universität Bochum

Nature Communications, 2020, vol. 11, issue 1, 1-8

Abstract: Abstract Established electrodecarboxylative etherification protocols are based on Hofer-Moest-type reaction pathways. An oxidative decarboxylation gives rise to radicals, which are further oxidised to carbocations. This is possible only for benzylic or otherwise stabilised substrates. Here, we report the electrodecarboxylative radical-radical coupling of lithium alkylcarboxylates with 1-hydroxybenzotriazole at platinum electrodes in methanol/pyridine to afford alkyl benzotriazole ethers. The substrate scope of this electrochemical radical coupling extends to primary and secondary alkylcarboxylates. The benzotriazole products easily undergo reductive cleavage to the alcohols. They can also serve as synthetic hubs to access a wide variety of functional groups. This reaction prototype demonstrates that electrodecarboxylative C–O bond formation can be taken beyond the intrinsic substrate limitations of Hofer-Moest mechanisms.

Date: 2020
References: Add references at CitEc
Citations: View citations in EconPapers (1)

Downloads: (external link)
https://www.nature.com/articles/s41467-020-18275-1 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:11:y:2020:i:1:d:10.1038_s41467-020-18275-1

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-020-18275-1

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().