α-Fluoroamine synthesis via P(iii)-mediated deoxygenative geminal fluorosulfonimidation of 1,2-diketones

Abstract

A deoxygenative geminal fluorosulfonimidation of 1,2-diketones was achieved for the synthesis of tetrasubstituted α-fluoroamines under mild conditions. In this study, a transition metal-free formal N–F insertion of N-fluorobenzenesulfonimide was enabled via the Kukhtin–Ramirez reaction employing a dealkylation-resistant P(III) reagent developed in our laboratory. Computational analysis was also performed to obtain a general mechanistic picture, which explained the reactivity and selectivity for this type of reaction.