Synthesis of gem-Difluoroalkenes via Zn-Mediated Decarboxylative/Defluorinative Cross-Coupling,Organic Letters

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Synthesis of gem-Difluoroalkenes via Zn-Mediated Decarboxylative/Defluorinative Cross-Coupling
Organic Letters ( IF 4.9 ) Pub Date : 2020-11-24 , DOI: 10.1021/acs.orglett.0c03554
Hai-Wu Du ₁ , Yang Chen ₁ , Jing Sun ₁ , Qi-Sheng Gao ₁ , He Wang ₁ , Ming-Dong Zhou ₁

Affiliation

An efficient and mild Zn-mediated decarboxylative/defluorinative alkylation of α-trifluoromethyl alkenes using N-hydroxyphthalimide esters as radical precursors was developed. Several α-trifluoromethyl alkenes were readily coupled to a wide range of primary, secondary, and tertiary radicals, affording the desired gem-difluoroethylenes in moderate to excellent yields. This reaction protocol was also successfully applied to the construction of complex molecules such as the bioactive natural dehydroabietic acid and glycosyl groups bearing the gem-difluoroethylene moiety.

中文翻译：

锌介导的脱羧/脱氟交叉偶联合成宝石-二氟烯烃

以N-羟基邻苯二甲酰亚胺酯为自由基前体，开发了一种高效温和的Zn介导的α-三氟甲基烯烃的脱羧/脱氟烷基化反应。几种α-三氟甲基烯烃易于与各种伯，仲和叔基团偶联，以中等至极好的收率提供了所需的宝石-二氟乙烯。该反应方案也已成功地用于复杂分子的构建，例如具有宝石-二氟乙烯部分的生物活性天然脱氢松香酸和糖基。

更新日期：2020-12-04

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