Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates

TETRAHEDRON

卷:92

Article

Zhu, Joshua L.¹  Scheidt, Karl A.¹ 

[1] Northwestern Univ, Dept Chem, 2145 Sheridan Rd, Evanston, IL 60208 USA

关键词: Photocatalysis;    N-Heterocyclic carbene;    Alkoxycarbonyl radical;    Esterification;    Radical-radical coupling;   

DOI  :  10.1016/j.tet.2021.132288

来源: Elsevier

【 摘 要 】

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.

【 授权许可】

Free