Catalytic 1,1-diazidation of alkenes

Wangzhen Qiu, Lihao Liao (), Xinghua Xu, Hongtai Huang, Yang Xu and Xiaodan Zhao ()
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Wangzhen Qiu: IGCME, Sun Yat-Sen University
Lihao Liao: IGCME, Sun Yat-Sen University
Xinghua Xu: IGCME, Sun Yat-Sen University
Hongtai Huang: IGCME, Sun Yat-Sen University
Yang Xu: IGCME, Sun Yat-Sen University
Xiaodan Zhao: IGCME, Sun Yat-Sen University

Nature Communications, 2024, vol. 15, issue 1, 1-12

Abstract: Abstract Compared to well-developed catalytic 1,2-diazidation of alkenes to produce vicinal diazides, the corresponding catalytic 1,1-diazidation of alkenes to yield geminal diazides has not been realized. Here we report an efficient approach for catalytic 1,1-diazidation of alkenes by redox-active selenium catalysis. Under mild conditions, electron-rich aryl alkenes with Z or E or Z/E mixed configuration can undergo migratory 1,1-diazidation to give a series of functionalized monoalkyl or dialkyl geminal diazides that are difficult to access by other methods. The method is also effective for the construction of polydiazides. The formed diazides are relatively safe by TGA-DSC analysis and impact sensitivity tests, and can be easily converted into various valuable molecules. In addition, interesting reactivity that geminal diazides give valuable molecules via the geminal diazidomethyl moiety as a formal leaving group in the presence of Lewis acid is disclosed. Mechanistic studies revealed that a selenenylation-deselenenylation followed by 1,2-aryl migration process is involved in the reactions, which provides a basis for the design of new reactions.

Date: 2024
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DOI: 10.1038/s41467-024-47854-9

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