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Updated: Sep 28, 2025

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Published on: June 10, 2021
α-Fluoroamine synthesis via P(III)-mediated deoxygenative geminal fluorosulfonimidation of 1,2-diketones
Yeri Son1, Sunjoo Hwang1, Sujin Bak1
1Department of Chemistry, Gwangju Institute of Science and Technology (GIST), 123 Cheomdan-gwagi-ro, Buk-gu, Gwangju 61005, Republic of Korea. junhochoi@gist.ac.kr.
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.
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