The photoredox-catalyzed 1,6-difluoromethylation of 3-methyl-4-nitro-5-styrylisoxazole
with HCF2SO2Na has been developed. Structurally
diverse difluoromethylated products were obtained in good yields,
and their further transformations were also investigated. The di-,
tri-, and monofluoromethylation of the substrates were compared, and
the yield of the difluoromethylation was the highest. DFT calculations
revealed that in the difluoromethylation reaction the CF2H radical was nucleophilic, and the transition state activation energy
was the lowest.
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