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Photoredox-Catalyzed Transfer Thio(poly)fluoroacyloxylation of Alkenes Using Oxime-Based Surrogates

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide An efficient photoredox-catalyzed strategy for two-component C(sp 3 )–S and C(sp 3 )–O bond formation using bench-stable and easy-to-handle oxime-based transfer reagents is reported. The distinct fragmentation pattern of these surrogates allows for a regioselective and redox-neutral 1,2-thio(poly)fluoroacyloxylation of unactivated alkenes and styrenes by a radical-polar crossover pathway, initiated by single-electron reduction of the surrogate. This method expands the utility of oxime-based surrogates in alkene difunctionalization, offering a versatile and scalable platform for the direct, chemo-, and regioselective synthesis of thio(poly)fluoroacyloxylated products with broad functional-group compatibility under mild conditions.

Source: ACS Catalysis

DOI: 10.1021/acscatal.5c07377

Authors: Sergiu Bicic, Velten S. E. Sobieraj, Sebastian Kemper, Hendrik F. T. Klare, Martin Oestreich

Institution: Technische Universität Berlin

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Deutsche Forschungsgemeinschaft, Einstein Stiftung Berlin, Technische Universität Berlin