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Synthesis of β-Thiolated-α-arylated Ketones Enabled by Photoredox and <i>N</i>-Heterocyclic Carbene-Catalyzed Radical Relay of Alkenes with Disulfides and Aldehydes

Hai‐Wu Du, Ming‐Shang Liu, Wei Shu

2022Organic Letters43 citationsDOI

Abstract

β-Thiolated-α-arylated ketones are perversive in bioactive molecules and serve as potential bidentate ligands for catalysis. Herein, a straightforward protocol to access β-thiolated ketones from aldehydes, alkenes, and disulfides enabled by the combination of photocatalysis and N-heterocyclic carbene catalysis is reported. The sequential radical addition to alkenes and subsequent radical–radical coupling cascade process simultaneously forge C–S and C–C bonds. The mild conditions allow for radical relay coupling with a broad functional group tolerance.

Topics & Concepts

ChemistryCarbeneCatalysisDenticityCombinatorial chemistryFunctional groupPhotochemistryOrganic chemistryMetalPolymerSulfur-Based Synthesis TechniquesRadical Photochemical ReactionsCatalytic C–H Functionalization Methods
Synthesis of β-Thiolated-α-arylated Ketones Enabled by Photoredox and <i>N</i>-Heterocyclic Carbene-Catalyzed Radical Relay of Alkenes with Disulfides and Aldehydes | Litcius