Work

Photoredox-Catalyzed Transfer Aminochlorination of Unactivated Alkenes Using Oxime-Based Surrogates

Year: 2025

Type: article

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

Source: ACS Catalysis

DOI: 10.1021/acscatal.5c01290

Authors: Sergiu Bicic, 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, University of Science and Technology of China