Stereoselective Synthesis of Fluoroalkanes via FLP Mediated Monoselective C─F Activation of Geminal Difluoroalkanes,Advanced Science

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Stereoselective Synthesis of Fluoroalkanes via FLP Mediated Monoselective C─F Activation of Geminal Difluoroalkanes
Advanced Science ( IF 14.3 ) Pub Date : 2023-10-31 , DOI: 10.1002/advs.202305768
Dániel Csókás _{1,

2} , Bivas Mondal ₁ , Miloš Đokić ₁ , Richa Gupta ₁ , Beatrice J Y Lee ₁ , Rowan D Young ₃

Affiliation

A method of desymmetrization of geminal difluoroalkanes using frustrated Lewis pair (FLP) mediated monoselective C–F activation where a chiral sulfide is the Lewis base component is reported. The stereoselective reaction provides generally high yields of diastereomeric sulfonium salts with dr of up to 95:5. The distribution of diastereomers is found to be thermodynamically controlled via facile sulfide exchange. The use of enantiopure chiral sulfides allows for high stereospecificity in nucleophilic substitution reactions and the formation of stereoenriched products.

中文翻译：

FLP介导的双二氟烷烃单选择性C─F活化立体选择性合成氟烷烃

报道了一种使用受阻路易斯对（FLP）介导的单选择性 C-F 活化对偕二氟烷烃进行去对称化的方法，其中手性硫化物是路易斯碱组分。立体选择性反应通常可提供高产率的非对映异构锍盐， dr高达 95:5。发现非对映异构体的分布是通过容易的硫化物交换进行热力学控制的。使用对映体纯手性硫化物可以在亲核取代反应中实现高立体特异性并形成立体富集的产物。

更新日期：2023-10-31

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