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

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1249-1253
Number of pages5
JournalOrganic letters
Volume22
Issue number4
DOIs
StatePublished - Feb 21 2020

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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