A mild and practical approach to N-CF3 secondary amines via oxidative fluorination of isocyanides

Jia-Luo Fu, Jun-Yunzi Wu, Juan-Fen Shi, Long-Ling Huang, Honggen Wang () and Qingjiang Li ()
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Jia-Luo Fu: Sun Yat-sen University
Jun-Yunzi Wu: Sun Yat-sen University
Juan-Fen Shi: Sun Yat-sen University
Long-Ling Huang: Sun Yat-sen University
Honggen Wang: Sun Yat-sen University
Qingjiang Li: Sun Yat-sen University

Nature Communications, 2025, vol. 16, issue 1, 1-10

Abstract: Abstract N-trifluoromethyl compounds, featuring a CF3 group directly attached to nitrogen, are valuable in medicinal chemistry. Despite substantial advances in their synthesis over the past decade, the efficient preparation of inherently unstable N-CF3 secondary amines remains a challenge in synthetic chemistry. Herein, we present a mild and practical method for synthesizing these compounds via oxidative fluorination of isocyanides using iodine as the oxidant, silver fluoride as the fluorinating reagent, and tert-butyldimethylsilane as the proton precursor. This approach benefits from simple workup, as all reagents and by-products can be easily removed through simple filtration and evaporation. This protocol features a broad substrate scope, good functional group tolerance, and good to excellent yields. Additionally, the resulting products can be readily converted into N-CF3 carbamoyl fluorides, valuable building blocks for the synthesis of diverse N-CF3 carbonyl derivatives.

Date: 2025
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DOI: 10.1038/s41467-025-60225-2

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