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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Copper-Catalyzed [3 + 2] Annulation of Azides with a (Difluorovinyl)zinc Complex, Fluoroacetylene Equivalent
Takeshi Fujita1, Masafumi Takeishi1, Junji Ichikawa1
1Division of Chemistry, Faculty of Pure and Applied Sciences, University of Tsukuba, Tsukuba, Ibaraki 305-8571, Japan.
Abstract:
The copper-catalyzed [3 + 2] annulation of organic azides with (2,2-difluorovinyl)zinc chloride-TMEDA was achieved via C-F bond cleavage. Thus, a series of 1-substituted 4-fluorotriazoles was synthesized in high yields. In this reaction, the difluorovinylzinc complex functions as an easy-to-handle equivalent of fluoroacetylene (FC≡CH) to undergo cycloaddition with azides. This work offers a facile and practical method for the use of fluoroacetylene, which has been considered to be highly reactive and difficult to handle and control for synthetic applications.
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