Dual Roles of Azide: Dearomative Dimerization of Furfuryl Azides.

A dearomative dimerization of furfuryl azides for the construction of furfuryl triazoles is developed. As a rare leaving group, azide is capable of initiating the generation of a furfuryl cation under the Lewis acid-catalyzed conditions, followed by reacting with the other azide to realize an intermolecular [3 + 2] cycloaddition/furan ring-opening cascade. By extending the reaction time, a fragmentation reaction of resulting furfuryl triazoles occurs to afford 1H-triazoles in high yield. Control studies demonstrated that key furfuryl cations also can be obtained from furfuryl triazoles. Furthermore, a chemoselective cross-cycloaddition can be achieved between furfuryl azides and a benzyl azide.

Citation

Zhe Hao, Penggang Zhao, Qingzhao Xing, Abdul Wahab, Ziwei Gao, Jing Gou, Binxun Yu. Dual Roles of Azide: Dearomative Dimerization of Furfuryl Azides. The Journal of organic chemistry. 2022 Aug 05;87(15):10185-10198

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PMID: 35864566

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