Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene,Journal of the American Chemical Society

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Vinyl Thianthrenium Tetrafluoroborate: A Practical and Versatile Vinylating Reagent Made from Ethylene
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2021-08-10 , DOI: 10.1021/jacs.1c06632
Fabio Juliá ₁ , Jiyao Yan ₁ , Fritz Paulus ₁ , Tobias Ritter ₁

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The use of vinyl electrophiles in synthesis has been hampered by the lack of access to a suitable reagent that is practical and of appropriate reactivity. In this work we introduce a vinyl thianthrenium salt as an effective vinylating reagent. The bench-stable, crystalline reagent can be readily prepared from ethylene gas at atmospheric pressure in one step and is broadly useful in the annulation chemistry of (hetero)cycles, N-vinylation of heterocyclic compounds, and palladium-catalyzed cross-coupling reactions. The structural features of the thianthrene core enable a distinct synthesis and reactivity profile, unprecedented for other vinyl sulfonium derivatives.

中文翻译：

乙烯基噻吩四氟硼酸盐：一种由乙烯制成的实用且多功能的乙烯基化试剂

乙烯基亲电子试剂在合成中的使用受到了阻碍，因为无法获得实用且具有适当反应性的合适试剂。在这项工作中，我们引入了乙烯基铪盐作为有效的乙烯基化试剂。这种实验室稳定的结晶试剂可以很容易地在大气压下一步由乙烯气体制备，并且广泛用于（杂）环的环化化学、杂环化合物的 N-乙烯基化和钯催化的交叉偶联反应。噻蒽核心的结构特征实现了独特的合成和反应特性，这是其他乙烯基锍衍生物前所未有的。

更新日期：2021-08-25

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