Taking Electrodecarboxylative Etherification Beyond Hofer-Moest Using a Radical C-O Coupling Strategy

Overview

Journal Nat Commun

Specialty Biology

Date 2020 Sep 4

PMID 32879323

Citations 6

Authors

Angel Manu Martinez

Davit Hayrapetyan

Tim van Lingen

Marco Dyga

Lukas J Goossen

Affiliations

Soon will be listed here.

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.

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