Radical-Mediated Methylenation of <i>N</i> -Heterocyclic Carboxylic Acids with DMSO to Access Exocyclic Olefinic Azacycles

A radical-mediated methylenation of <i>N</i>-heterocyclic carboxylic acids with DMSO is developed using KF as a catalyst, which allows efficient access to exocyclic olefinic azacycles. This novel strategy features transition metal-free conditions, the direct use of DMSO as a methylene source, and a free-radical cascade process.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-02-25
DOI
https://doi.org/10.1021/acs.joc.5c03092
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Radical-Mediated Methylenation of N -Heterocyclic Carboxylic Acids with DMSO to Access Exocyclic Olefinic Azacycles

Kaiping Hou, Lishou Yang, T Deng, Lanfeng He et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Radical-Mediated Methylenation of N -Heterocyclic Carboxylic Acids with DMSO to Access Exocyclic Olefinic Azacycles

Kaiping Hou, Lishou Yang, T Deng, Lanfeng He, Enhua Wang, Xiaosheng Yang, Lang Zhou, Linlin Dai, Xiong Pan
article en

Abstract

A radical-mediated methylenation of <i>N</i>-heterocyclic carboxylic acids with DMSO is developed using KF as a catalyst, which allows efficient access to exocyclic olefinic azacycles. This novel strategy features transition metal-free conditions, the direct use of DMSO as a methylene source, and a free-radical cascade process.

The Journal of Organic ChemistryVol. 91(10)
Guiyang Medical University (CN), State Administration of Traditional Chinese Medicine of the People's Republic of China (CN), Agriculture and Food (AU)
Openalex Percentile: Top 42%
Catalytic C–H Functionalization Methods
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