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Photocatalytic Aerobic Oxysulfonylation of Alkynes to Access <scp>β‐Keto</scp> Sulfones Catalyzed by <scp>OVs‐N‐Nb<sub>2</sub>O<sub>5</sub></scp>

Tao Song, Yinpan Zhang, Chun Wang, Yafei Li, Yong Yang

2022Chinese Journal of Chemistry12 citationsDOI

Abstract

Comprehensive Summary Herein, we report a novel heterogeneous photocatalyst for radical‐mediated oxidative oxysulfonylation of alkynes to β‐keto sulfones under environmentally benign conditions. The oxygen vacancy‐rich semiconductor Nb 2 O 5 (labeled as OVs‐N‐Nb 2 O 5 ) could efficiently catalyze a wide range of alkynes, especially for those bearing electron‐deficient substituents or internal alkynes, to their corresponding β‐keto sulfones in good to high yields with good tolerance of diverse functional groups under visible‐light illumination. The late‐stage modification of steroidal compounds and synthesis of bioactive molecules were also achieved via this procedure, highlighting its potential for practical applications. Meanwhile, the photocatalyst OVs‐N‐Nb 2 O 5 showed outstanding catalytic stability for successive recycles without appreciable loss in activity and selectivity. The critical role of oxygen vacancies on improving reaction activity and selectivity was clearly disclosed via control experiments and theoretical calculation.

Topics & Concepts

ChemistryCatalysisSelectivityPhotocatalysisOxygenPhotochemistryMoleculeMolecular oxygenCombinatorial chemistryOxidative phosphorylationOrganic chemistryBiochemistrySulfur-Based Synthesis TechniquesAdvanced Photocatalysis TechniquesChemical Synthesis and Reactions
Photocatalytic Aerobic Oxysulfonylation of Alkynes to Access <scp>β‐Keto</scp> Sulfones Catalyzed by <scp>OVs‐N‐Nb<sub>2</sub>O<sub>5</sub></scp> | Litcius