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Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates.

ABSTRACT: 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-heterocyclic 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.

SUBMITTER: Zhu JL

PROVIDER: S-EPMC8274565 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates.

Zhu Joshua L JL Scheidt Karl A KA

Tetrahedron 20210616

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 <i>N</i>-heterocyclic carbene catalysis and photocatalysis, we have prepared dimethylimidazolium esters that can function as an alkoxycarbonyl radical surrogate under photocatalytic conditions. We demonstra ...[more]

PMID: 34262231

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