Selective Denitrificative Fluorination and Desulfurative Fluorination Controlled by AgF/AgF2
Yali Long1,2, Xingjin He1, Linbei Deng3
1Department of Nuclear Medicine, First Affiliated Hospital of Sun Yat-sen University, Guangzhou, Guangdong510080, China.
Abstract:
The development of novel N-fluoroalkylated phosphoramidates will enrich the toolbox of organophosphorus chemistry. Here, we report the synthesis of [19F]/[18F] phosphoramidofluoridates and N-CF3 phosphoramidates via two controllable fluorinations of phenyl phosphorylcarbamodithioate (substrate S): S underwent selective P-N bond cleavage to access phosphoramidofluoridates by silver(I) fluoride and successive desulfurative fluorination to access N-CF3 phosphoramidates by silver(II) fluoride. Moreover, the desulfurative fluorination strategy can be extended to the preparation of N-CF2H, N-C2F5, and N-CF2OPh phosphoramidates.
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