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FSO2N3-Enabled Synthesis of Tetrazoles from Amidines and Guanidines
Tianyu Wang1, Long Xu2, Jiajia Dong2,3,4
1Laboratory of Organofluorine Chemistry Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China.
Abstract:
Herein we report the facile syntheses of tetrazoles enabled by FSO2N3 under mild conditions. FSO2N3 has been shown as the most powerful diazotizing reagent, which converts thousands of primary amines to azides fast and orthogonally. As the follow-up studies of the diazo transfer reaction using FSO2N3, we discover that amidines and guanidines are rapidly transformed into tetrazole derivatives when reacting with FSO2N3 under an aqueous environment, which is unprecedented for tetrazole synthesis.
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