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Published on: January 19, 2016
Direct 1,6-Difluoromethylation of 3-Methyl-4-nitro-5-styryl Isoxazoles by Photoredox-Promoted Radical Addition
Jianli Zheng1,2, Yingqian Xu1, Shaorui Song1
1School of Pharmaceutical and Chemical Engineering, Taizhou University, 1139 Shifu Road, Taizhou 318000, China.
Abstract:
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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