Pentafluorophenyl Esters: Highly Chemoselective Ketyl Precursors for the Synthesis of α,α-Dideuterio Alcohols Using SmI2 and D2O as a Deuterium Source

Hengzhao Li; Yuxia Hou; Chengwei Liu; Zemin Lai; Lei Ning; Roman Szostak; Michal Szostak; Jie An

doi:10.1021/acs.orglett.9b04383

Pentafluorophenyl Esters: Highly Chemoselective Ketyl Precursors for the Synthesis of α,α-Dideuterio Alcohols Using SmI₂ and D₂O as a Deuterium Source

Org Lett. 2020 Feb 21;22(4):1249-1253. doi: 10.1021/acs.orglett.9b04383. Epub 2020 Jan 8.

Authors

Hengzhao Li¹, Yuxia Hou¹, Chengwei Liu², Zemin Lai¹, Lei Ning¹, Roman Szostak³, Michal Szostak², Jie An¹

Affiliations

¹ College of Science , China Agricultural University , Beijing 100193 , China.
² Department of Chemistry , Rutgers University , 73 Warren Street , Newark , New Jersey 07102 , United States.
³ Department of Chemistry , Wroclaw University , F. Joliot-Curie 14 , Wroclaw 50-383 , Poland.

PMID: 31913049
DOI: 10.1021/acs.orglett.9b04383

Abstract

We report the first highly chemoselective synthesis of α,α-dideuterio alcohols with exquisite incorporation of deuterium (>98% [D₂]) using pentafluorophenyl esters as ketyl radical precursors, SmI₂ as a mild reducing agent, and D₂O as the deuterium source. This system tolerates a variety of functional groups, offering rapid entry to valuable α,α-dideuterated alcohol building blocks. More generally, this report introduces pentafluorophenyl esters as the most reactive O-ketyl precursors reported to date.