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Our group has recently developed α-fluoroamine synthesis using dioxaphospholenes derived from various 1,2-diketones and the dealkylation-resistant phosphoramidite as carbene surrogates that enabled the formal insertion into the N–F bond of (PhSO2)2NF. This full account presents the scope and limitation in terms of the reactivity and the site-selectivity, which were rationalized through the computational analysis. In addition, the efforts to broaden the synthetic utility of the current process by incorporating other nitrogen nucleophiles and halogen electrophiles are described.

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