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.
Highlights
Established electrodecarboxylative etherification protocols are based on Hofer-Moest-type reaction pathways
Anodic oxidation of carboxylic acids induces their decarboxylation with the formation of carboncentred radicals, which swiftly undergo homocoupling with formation of alkanes[39,40,41]
In conclusion, this work provides the proof of concept for an electrodecarboxylative radical combination approach to C–O bond formation
Summary
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. The benzotriazole products undergo reductive cleavage to the alcohols They can 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. Decarboxylative C–O bond formation is a attractive synthetic strategy since carboxylic acids are widely available in great structural diversity[4]. High selectivity can only be achieved if the radical and the positive a
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