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

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Copper-Catalyzed [3 + 2] Annulation of Azides with a (Difluorovinyl)zinc Complex, Fluoroacetylene Equivalent
Organic Letters ( IF 4.9 ) Pub Date : 2020-11-23 , DOI: 10.1021/acs.orglett.0c03476
Takeshi Fujita ₁ , Masafumi Takeishi ₁ , Junji Ichikawa ₁

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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.

中文翻译：

铜催化的[3 + 2]叠氮化物与（二氟乙烯基）锌络合物，氟乙炔当量的环化

通过C-F键裂解，实现了铜的有机叠氮化物与（2,2-二氟乙烯基）氯化锌-TMEDA的铜环化[3 + 2]。因此，高产率地合成了一系列的1-取代的4-氟三唑。在该反应中，二氟乙烯基锌络合物起易于处理的氟乙炔（FC≡CH）的作用，与叠氮化物进行环加成反应。这项工作为使用氟乙炔提供了一种简便实用的方法，该方法已被认为具有很高的反应活性，对于合成应用而言难以处理和控制。

更新日期：2020-12-04

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