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Synfacts 2025; 21(08): 813
DOI: 10.1055/a-2639-3851
Polymer-Supported Synthesis

Oxidative Nitrogenation of Alkenes through C=C Bond Cleavage Using a Zeolite-Supported Copper Catalyst

Contributor(s):
Yasuhiro Uozumi 
,
Kenji Tsukamoto
Cheng Z, Huang K, Wang C, Chen L, Li X, Hu Z, Shan X, Cao P-F, Sun H, Chen W, Li C, Zhang Z, Tan H, Jiang X, Zhang G, Zhang Z, Lin M, Wang L, Zheng A, Xia C *, Wang T, Song S, Shu X, Jiao N *. Peking University, Research Institute of Petroleum Processing, and Changping Laboratory, Beijing, P. R. China
Catalytic Remodeling of Complex Alkenes to Oxonitriles through C=C Double Bond Deconstruction.

Science 2025;
387: 1083-1090
DOI: 10.1126/science.adq8918
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Keywords

copper catalysis - zeolites - aerobic nitrogenation - C–C double bond cleavage - alkenes - oxonitriles

Significance

A hierarchical titanium silicalite-1 (h-TS-1) zeolite-supported Cu catalyst, CuO/h-TS-1, was prepared according to equation 1. CuO/h-TS-1 promoted the oxidative nitrogenation of alkenes with azidotrimethylsilane (2) in MeCN under O2 at 60 °C for 24 hours to give the corresponding oxonitriles 3 (55 examples) in up to 92 % yield (Eq. 2).


 

Comment

In the reaction of 1-phenylcyclohexene (1d), the catalyst was recovered by filtration and reused six times without a significant loss of its catalytic activity (fresh: 90 %, 7th: 87 %). When the reactions were carried out at 20 °C in the presence of water, β-azido peroxy alcohols (5 examples) were obtained in up to 82 % yield (Eq. 3).


 

 

Publication History

Article published online:
23 July 2025

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