Tetrahedron ( IF 2.1 ) Pub Date : 2021-06-16 , DOI: 10.1016/j.tet.2021.132288 Joshua L Zhu 1 , Karl A Scheidt 1
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.
中文翻译:
光催化酰基唑鎓促进三氟硼酸盐的烷氧基羰基化
尽管最近在有机自由基物种的选择性产生和偶联方面取得了进展,但相对于其他含碳自由基物种,烷氧羰基自由基仍未得到充分探索。从利用双N-杂环卡宾催化和光催化生成酰基自由基等价物的新策略中汲取灵感,我们制备了可在光催化条件下用作烷氧基羰基自由基替代物的二甲基咪唑鎓酯。我们通过制备由这种自由基替代物与氧化生成的烷基自由基偶联产生的酯,证明了这些基于唑鎓的伙伴的合成效用。