Radical Oxyazidation of Alkenes in Pure Water

Jinfeng Cui; Huan Zhou; Yajun Li; Hongli Bao

doi:10.1055/a-1804-8859

Synthesis, Table of Contents

Synthesis 2022; 54(14): 3262-3270
DOI: 10.1055/a-1804-8859

paper

Radical Oxyazidation of Alkenes in Pure Water

Authors

Jinfeng Cui

^aCollege of Chemistry, Fuzhou University, Fuzhou, Fujian 350108, P. R. of China

^bKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, P. R. of China
Huan Zhou∗

^bKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, P. R. of China
Yajun Li∗

^bKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, P. R. of China
Hongli Bao

^bKey Laboratory of Coal to Ethylene Glycol and Its Related Technology, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002, P. R. of China

^cUniversity of Chinese Academy of Sciences, Beijing 100049, P. R. of China

Abstract

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Abstract

Compared to universal radical difunctionalizations of alkenes that are performed with organic solvents, such reactions with water as the sole solvent are rarely reported. Concerning the global consensus on environmental issues, we have developed herein a method for the radical oxyazidation of alkenes in pure water. This reaction allows the construction of C–N and C–O bonds in a one-pot process. Styrenes, 1,3-dienes, and unactivated alkenes react smoothly under mild and environmentally benign conditions to afford a wide scope of functionalized azides in excellent yields and selectivities.

Key words

radicals - oxyazidation - alkenes - water - TEMPO - copper

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References

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