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

Chem Commun (Camb). 2021 May 25;57(42):5195-5198. doi: 10.1039/d1cc01381e. Epub 2021 Apr 28.

Authors

Hengzhao Li¹, Mengqi Peng², Zemin Lai², Lei Ning², Xingyue Chen², Xiaoxu Zhang³, Pengjie Wang³, Roman Szostak⁴, Michal Szostak⁵, Jie An³

Affiliations

¹ Department of Nutrition and Health, China Agricultural University, Beijing 100193, China. jie_an@cau.edu.cn and Department of Chemistry and Innovation Center of Pesticide Research, China Agricultural University, Beijing 100193, China.
² Department of Chemistry and Innovation Center of Pesticide Research, China Agricultural University, Beijing 100193, China.
³ Department of Nutrition and Health, China Agricultural University, Beijing 100193, China. jie_an@cau.edu.cn.
⁴ Department of Chemistry, Wroclaw University, F. Joliot-Curie 14, Wroclaw 50-383, Poland.
⁵ Department of Chemistry, Rutgers University, 73 Warren Street, Newark, New Jersey 07102, USA. michal.szostak@rutgers.edu.

PMID: 33908475
DOI: 10.1039/d1cc01381e

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.