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Copper-Catalyzed [3 + 2] Annulation of Azides with a (Difluorovinyl)zinc Complex, Fluoroacetylene Equivalent

Takeshi Fujita, Masafumi Takeishi and Junji Ichikawa*

*Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan, Email: junjichem.tsukuba.ac.jp

T. Fujita, M. Takeishi, J. Ichikawa, Org. Lett., 2020, 22, 9253-9257.

DOI: 10.1021/acs.orglett.0c03476 (free Supporting Information)


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Abstract

A copper-catalyzed [3 + 2] annulation of organic azides with (2,2-difluorovinyl)zinc chloride-TMEDA provides 1-substituted 4-fluorotriazoles in high yields via C-F bond cleavage. The difluorovinylzinc complex functions as an easy-to-handle equivalent of the highly reactive and difficult to handle fluoroacetylene (FC≡CH).

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Key Words

1,2,3-triazoles


ID: J54-Y2020