Recent Advances in Transition Metal-Catalyzed Functionalization of gem-Difluoroalkenes.,Israel Journal of Chemistry

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Recent Advances in Transition Metal-Catalyzed Functionalization of gem-Difluoroalkenes.
Israel Journal of Chemistry ( IF 2.3 ) Pub Date : 2020-03-10 , DOI: 10.1002/ijch.201900173
Suvajit Koley ₁ , Ryan A Altman ₁

Affiliation

gem‐Difluorinated alkenes are readily accessible building blocks that can undergo functionalization to provide a broad spectrum of fluorinated and non‐fluorinated products. Herein, we review recent (since 2017) transition metal‐catalyzed transformations of these specialized alkenes and summarize general reactivity patterns of these reactions. Many transition metal‐catalyzed reactions undergo net C−F bond functionalization reactions to deliver monofluorinated products. These reactions typically proceed through β‐fluoroalkylmetal intermediates that readily eliminate a β‐fluoride to deliver monofluoroalkene products. A second series of reactions exploit coinage metal fluorides to add F⁻ to the gem‐difluorinated alkene, and further functionalization delivers trifluoromethyl‐containing products. In stark contrast, few transition metal‐catalyzed reactions proceed in net “fluorine‐retentive processes” to deliver difluoromethylene‐based products.

中文翻译：

过渡金属催化宝石二氟烯烃官能化的最新进展。

gem -二氟化烯烃是易于获得的结构单元，可以进行功能化以提供广泛的氟化和非氟化产品。在此，我们回顾了最近（自 2017 年以来）过渡金属催化的这些特殊烯烃的转化，并总结了这些反应的一般反应模式。许多过渡金属催化的反应都会发生净 C−F 键官能化反应，以产生单氟化产物。这些反应通常通过β-氟烷基金属中间体进行，该中间体很容易消除β-氟化物以产生单氟烯烃产物。第二系列反应利用造币金属氟化物将 F ^-添加到宝石二氟化烯烃中，并进一步官能化产生含三氟甲基的产物。形成鲜明对比的是，很少有过渡金属催化的反应在净“氟保留过程”中进行以产生基于二氟亚甲基的产品。

更新日期：2020-03-10

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