Visible light-promoted oxycarbonylation of unactivated alkenes†

EES catalysis Pub Date : 2024-08-20 DOI:10.1039/D4EY00149D
Hefei Yang, Yuanrui Wang, Le-Cheng Wang and Xiao-Feng Wu
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Abstract

Oxygen-centered radicals are highly reactive and have played a key role in organic transformations since their discovery. Nowadays, the direct difunctionalization of alkenes involving oxygen-centered radicals is still underdeveloped due to the inherent properties of oxygen-centered radicals, especially the intermolecular radical addition of unactivated alkenes. Herein, we report an intermolecular oxygen-centered radical addition carbonylation reaction of unactivated alkenes under visible light irradiation. The transformation was initiated with the direct addition of alkoxycarbonyloxy radicals to alkenes, which then underwent aromatic migration under the intervention of carbon monoxide to achieve the targeted oxycarbonylation products.

Abstract Image

Abstract Image

可见光促进未活化烯烃的氧羰基化反应
氧中心自由基具有高活性,自发现以来一直在有机转化中发挥着关键作用。目前,由于氧中心自由基的固有特性,特别是未活化烯烃的分子间自由基加成,涉及氧中心自由基的烯烃直接双官能化反应仍不发达。在此,我们报告了在可见光照射下未活化烯烃的分子间氧心自由基加成羰基化反应。该转化是通过烷氧基羰氧自由基直接加成到烯中而开始的,然后在一氧化碳的干预下发生芳香迁移,从而得到目标氧羰基化产物。
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