Sulfone as traceless activating group: Divergent synthesis of α-fluoroamides with C–F quaternary stereocenters

Jieqing Wu , Liying Fu , Renyi Diao , Longjun Nie , Chi Zhang , Yufeng Li , Chao Feng
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Abstract

A novel approach to α-fluoroamides bearing a C–F quaternary stereocenter is reported herein. With sulfone installed as the activating group, an alkyl group as well as a fluorine atom was introduced successively under mild conditions. Subsequently, heterolytic fission of the C–S bond occurred smoothly under photoredox conditions to afford a tertiary radical, which then engaged in varied intramolecular cyclizations depending on substrate structure and condition applied, rendering sulfone an overall traceless activating group.

Abstract Image

作为无迹激活基团的砜:含C-F季立体中心的α-氟酰胺的发散合成
本文报道了一种合成含C-F季立体中心α-氟酰胺的新方法。以砜为活化基团,在温和条件下依次引入烷基和氟原子。随后,C-S键在光氧化还原条件下顺利发生异裂变,产生三级自由基,然后根据底物结构和应用条件进行不同的分子内环化,使砜成为一个总体上不可见的激活基团。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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CiteScore
14.40
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