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Synlett
DOI: 10.1055/a-2803-0545
Synpacts

Unlocking Difluorocarbene as a Versatile Precursor to Fluorocarbon Anions and Radicals via Palladium Catalysis

Authors

  • Shi-Ping Sun

    1   State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry Chinese Academy of Sciences, Shanghai, China (Ringgold ID: RIN58309)

  • Xingang Zhang 

    2   State Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China

Supported by: Strategic Priority Research Program of the Chinese Academy of Sciences XDB0590000
Supported by: National Natural Science Foundation of China 22193072
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Difluorocarbene, a versatile bipolar intermediate, has been widely exploited in ionic-type coupling reactions. Its direct transformation into a fluorinated carbon-radical species, however, has remained a formidable challenge because of the large singlet-triplet energy gap. Here we report an unprecedented strategy that unlocks difluorocarbene as a precursor for both fluorinated carbanions and carbon radicals through the thermolytic homolysis of an aryldifluoromethylpalladium intermediate. This palladium-catalyzed sequential process enables a modular three-component coupling of aryl iodides, alkenes, and ClCF 2 H, delivering a broad spectrum of difluoroalkylated arenes in high efficiency. The method features inexpensive and readily available reagents, excellent functional-group tolerance, and opens a new avenue for the precise installation of the difluoromethylene motif.



Publication History

Received: 15 December 2025

Accepted after revision: 02 February 2026

Accepted Manuscript online:
05 February 2026

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