Metal-free para-selective C-H amination and azidation of N-arylhydroxylamines

Yaru Bai, Hui-Mei Jiang, Wenbo Xu, Li-Ping Xu () and Hongyin Gao ()
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Yaru Bai: Ji′nan
Hui-Mei Jiang: Ji′nan
Wenbo Xu: Ji′nan
Li-Ping Xu: Ji′nan
Hongyin Gao: Ji′nan

Nature Communications, 2025, vol. 16, issue 1, 1-12

Abstract: Abstract Due to the universality of arylamine and arylazide building blocks in pharmaceuticals, natural products and functional materials, the formation of aryl C-N bonds from readily available materials appears to be highly appealing, especially for the exclusive regioselective C-H amination. Despite substantial advancements in the synthesis of aryl C-N bonds, achieving a general, efficient, and para-selective C-H amination under mild conditions remains a significant challenge. Here we showcase a fluorosulfuryl imidazolium triflate-mediated para-selective C-H amination of N-arylhydroxylamines employing primary and secondary amines, diphenylmethanimine and azides as nitrogen source, affording structurally diverse 1,4-diaminoarenes or para-azidoanilides in the absence of oxidants and transition-metal catalysts. This effective protocol exhibits exclusive para-selectivity and good functional group tolerance for both N-arylhydroxylamines and N-nucleophiles (>90 examples). DFT calculations have been performed to elucidate the high chemoselectivity observed amidst multiple nucleophilic and electrophilic species.

Date: 2025
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DOI: 10.1038/s41467-025-63534-8

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