Acyl fluorides as direct precursors to fluoride ketyl radicals: reductive deuteration using SmI2 and D2O

Hengzhao Li; Mengqi Peng; Zemin Lai; Lei Ning; Xingyue Chen; Xiaoxu Zhang; Pengjie Wang; Roman Szostak; Michal Szostak; Jie An

doi:10.1039/D1CC01381E

Acyl fluorides as direct precursors to fluoride ketyl radicals: reductive deuteration using SmI₂ and D₂O†

Hengzhao Li,

^ab Mengqi Peng,

^b Zemin Lai,^b Lei Ning,

^b Xingyue Chen,^b Xiaoxu Zhang,^a Pengjie Wang,^a Roman Szostak,

^c Michal Szostak

*^d and Jie An

*^a

Author affiliations

* Corresponding authors

^a Department of Nutrition and Health, China Agricultural University, Beijing 100193, China
E-mail: jie_an@cau.edu.cn

^b Department of Chemistry and Innovation Center of Pesticide Research, China Agricultural University, Beijing 100193, China

^c Department of Chemistry, Wroclaw University, F. Joliot-Curie 14, Wroclaw 50-383, Poland

^d Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, USA
E-mail: michal.szostak@rutgers.edu

Abstract

A highly chemoselective reductive deuteration of acyl fluorides to provide α,α-dideuterio alcohols with exquisite levels of deuterium incorporation was developed using SmI₂ and D₂O as the deuterium source. This method introduces acyl fluorides as attractive radical precursors for the generation of reactive acyl-type fluoride ketyls that should find widespread application in many synthetic strategies involving single electron transfer processes.

Chemical Communications

Acyl fluorides as direct precursors to fluoride ketyl radicals: reductive deuteration using SmI₂ and D₂O†

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Acyl fluorides as direct precursors to fluoride ketyl radicals: reductive deuteration using SmI₂ and D₂O

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