Visible-light-induced acridinium-catalyzed selective <i>N</i>-dealkylation of N-heterocycles

We have developed an efficient and general strategy for <i>N</i>-chlorosuccinimide (NCS)-promoted <i>N</i>-dealkylation of aza-heterocycles <i>via</i> acridinium-photocatalyzed electron transfer and hydrogen atom transfer. This approach effectively obviates the need for transition metal catalysis and features wide substrate scope as well as exclusive chemo-selectivity. Remarkably, the method allowed the deprotection of the privileged but stable <i>N</i>-alkyl group, thus filling a gap in the practical <i>N</i>-dealkylation of N-heteroaromatics.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc00609k
Citations
1
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.94
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article

Visible-light-induced acridinium-catalyzed selective N-dealkylation of N-heterocycles

Xianying Zhou, Yaoyao Zhang, Lin‐Yu Jiao, Shanshan Liu
1 citations
Chemical Communications
Radical Photochemical Reactions
0.94
article

Visible-light-induced acridinium-catalyzed selective N-dealkylation of N-heterocycles

Xianying Zhou, Yaoyao Zhang, Lin‐Yu Jiao, Shanshan Liu
article en
1 citations

Abstract

We have developed an efficient and general strategy for <i>N</i>-chlorosuccinimide (NCS)-promoted <i>N</i>-dealkylation of aza-heterocycles <i>via</i> acridinium-photocatalyzed electron transfer and hydrogen atom transfer. This approach effectively obviates the need for transition metal catalysis and features wide substrate scope as well as exclusive chemo-selectivity. Remarkably, the method allowed the deprotection of the privileged but stable <i>N</i>-alkyl group, thus filling a gap in the practical <i>N</i>-dealkylation of N-heteroaromatics.

Chemical CommunicationsVol. 61(41)
Northwest University (CN), Shaanxi University of Science and Technology (CN)
Openalex Percentile: Top 27%
Radical Photochemical Reactions
0.94
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