One-pot three-component synthesis, structure and redox properties of ferrocenyl isoxazoles

A consecutive coupling-cycloaddition sequence of acid chlorides, terminal alkynes, and in situ generated nitrile oxides furnishes ferrocenyl substituted redox active isoxazoles in moderate to good yields. The structure was unambiguously assigned by X-ray structure analyses and the electronic structure was elucidated by computational methods. Redox potentials of all representatives are strongly effected by the electronic nature of the bridging isoxazoloyl moiety.

Graphical abstractA consecutive coupling-cycloaddition sequence of acid chlorides, terminal alkynes, and in situ generated nitrile oxides furnishes ferrocenyl substituted redox active isoxazoles in moderate to good yields. Redox potentials of all representatives are strongly effected by the electronic nature of the bridging isoxazoloyl moiety.Figure optionsDownload full-size imageDownload as PowerPoint slide