Visible‐Light Photoredox‐Catalyzed Ring‐Opening Carboxylation of Cyclic Oxime Esters with CO<sub>2</sub>
Yuan‐Xu Jiang, Liang Chen, Chuan‐Kun Ran, Lei Song, Wei Zhang, Li‐Li Liao, Da‐Gang Yu
Abstract
The carboxylation of cyclic oxime esters with carbon dioxide via visible-light photoredox catalysis is demonstrated for the first time. A variety of cyclic oxime esters undergo ring-opening C-C bond cleavage and carboxylation to give cyanoalkyl-containing carboxylic acids in moderate to good yields. Moreover, this methodology features mild reaction conditions (room temperature, 1 atm), wide substrate scope, good functional group tolerance as well as facile derivations of products. Mechanistic studies indicate that the benzylic radicals and anions might be the key intermediates.
Topics & Concepts
CarboxylationOximeChemistryCatalysisPhotochemistryFunctional groupSubstrate (aquarium)RadicalRing (chemistry)Bond cleavageOrganic chemistryCombinatorial chemistryPolymerOceanographyGeologyCarbon dioxide utilization in catalysisCO2 Reduction Techniques and CatalystsRadical Photochemical Reactions