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Updated: Apr 24, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Difluorocarbene/DMSO: A Polarity-Reversing Reagent Allowing Electrophilic Arene Halogenation with Halides
Jun He1, Hao-Lin Niu1, Jia-Shu Yan1
1Key Laboratory of Synthetic and Biological Colloids, Ministry of Education, School of Chemical and Material Engineering, Jiangnan University, Wuxi 214122, P. R. China.
Abstract:
This study presents an unconventional arene halogenation strategy facilitated by a difluorocarbene precursor in conjunction with a DMSO solvent. The difluorocarbene/DMSO system enables a reversal of halide polarity, generating a key halosulfonium intermediate in situ that engages in electrophilic aromatic substitution with arenes. This method operates under mild and neutral conditions without requiring transition-metal catalysts or conventional reactive halogenating reagents. This study reveals a novel reactivity mode of difluorocarbene and may stimulate efforts to extend the application of the difluorocarbene/DMSO strategy.
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