Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates

Despite recent advancements in the selective generation and coupling of organic radical species, the alkoxycarbonyl radical remains underexplored relative to other carbon-containing radical species. Drawing inspiration from new strategies for generating acyl radical equivalents utilizing dual N-het-erocyclic carbene catalysis and photocatalysis, we have prepared dimethylimidazolium esters that can function as an alkoxycarbonyl radical surrogate under photocatalytic conditions. We demonstrate the synthetic utility of these azolium-based partners through the preparation of esters arising from the coupling of this radical surrogate with an oxidatively generated alkyl radical. (c) 2021 Elsevier Ltd. All rights reserved.

Automated summary

Despite recent advancements in the selective generation and coupling of organic radical species, the alkoxycarbonyl radical remains underexplored relative to other carbon-containing radical species. Inspired by strategies using dual N-heterocyclic carbene catalysis and photocatalysis, dimethylimidazolium esters were prepared as alkoxycarbonyl radical surrogates under photocatalytic conditions, showing synthetic utility in coupling with an oxidatively generated alkyl radical to form esters.