Photoredox-catalyzed transfer aminochlorination of unactivated alkenes using oxime-based surrogates

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.

Publication Details

Journal
DepositOnce
Published
2025-04-04
DOI
https://doi.org/10.14279/depositonce-23603
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Photoredox-catalyzed transfer aminochlorination of unactivated alkenes using oxime-based surrogates

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Radical Photochemical Reactions
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Photoredox-catalyzed transfer aminochlorination of unactivated alkenes using oxime-based surrogates

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Abstract

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.

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Radical Photochemical Reactions
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