Hypervalent Iodine–Catalyzed Cycloaddition of Nitrile Oxides to Alkenes

Abstract

A new and convenient method for preparation of isoxazolines was developed by a catalytic cycloaddition of nitrile oxides generated in situ from aldoximes to alkenes in the presence of a catalytic amount of iodobenzene. In this protocol, iodobenzene was first oxidized into the hypervalent iodine intermediate by m-chloroperbenzoic acid, which then transformed aldoximes into nitrile oxides, and a 1,3-dipolar cycloaddition of nitrile oxides to alkenes to provide the isoxazolines in moderate to good yields.

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GRAPHICAL ABSTRACT

Keywords:

• Catalytic reaction
• cycloaddition
• hypervalent iodine intermediate
• iodobenzene
• isoxazoline

ACKNOWLEDGMENT

Financial support from the Natural Science Foundation of China (Project 21072176) is greatly appreciated.

Notes

^a Isolated yield.

^a Isolated yield.