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

An efficient photoredox-catalyzed strategy for simultaneous C(sp3)–N and C(sp3)–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.

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Publication Details

Journal
ACS Catalysis
Published
2025-04-04
DOI
https://doi.org/10.1021/acscatal.5c01290
Citations
7
Primary Topic
Synthesis and Catalytic Reactions
Type
article
Field-Weighted Citation Impact
6.55

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article

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

Martin Oestreich, Sergiu Bicic, Hendrik F. T. Klare
7 citations
ACS Catalysis
Synthesis and Catalytic Reactions
6.55
article

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

Martin Oestreich, Sergiu Bicic, Hendrik F. T. Klare
article en
7 citations

Abstract

An efficient photoredox-catalyzed strategy for simultaneous C(sp3)–N and C(sp3)–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.

ACS CatalysisVol. 15(8)
Technische Universität Berlin (DE)
Deutsche Forschungsgemeinschaft, Einstein Stiftung Berlin
Zero hunger
Openalex Percentile: Top 3%
Synthesis and Catalytic Reactions
6.55
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