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Synthesis 2023; 55(10): 1533-1542
DOI: 10.1055/a-2005-4296
DOI: 10.1055/a-2005-4296
paper
Tandem Deoxygenative Geminal Fluorosulfonimidation of 1,2-Diketones via Formal N–F Insertion Enabled by Dealkylation-Resistant Phosphoramidite
This research was supported by the National Research Foundation of Korea (NRF) funded by the Ministry of Science and ICT (NRF-2020R1F1A1076028 and NRF-2022R1A2C1007351).
Abstract
Our group has recently developed an α-fluoroamine synthesis using dioxaphospholenes derived from various 1,2-diketones and the dealkylation-resistant phosphoramidite as carbene surrogates, enabling the formal insertion into the N–F bond of (PhSO2)2NF. This full account presents the scope and limitations in terms of the reactivity and the site selectivity; these were rationalized through 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.
Key words
fluoroamine - sulfonimide - dioxaphospholene - carbene surrogate - phosphoramidite - N–F insertion - geminal difunctionalization - 1,2-diketoneSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2005-4296.
- Supporting Information
Publication History
Received: 04 November 2022
Accepted after revision: 31 December 2022
Accepted Manuscript online:
31 December 2022
Article published online:
02 February 2023
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For recent applications of the Kukhtin–Ramirez reaction, see:
See also: