Deoxytrifluoromethylation of Alcohols

Nicholas E. Intermaggio, Agustin Millet, Dali L. Davis, David W.C. MacMillan

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Deoxy-functionalization of alcohols represents a class of reactions that has had a profound impact on modern medicine. In particular, deoxyfluorination is commonly employed as a means to incorporate high-value fluorine atoms into drug-like molecules. Recently, the trifluoromethyl (CF3) group has garnered attention from medicinal chemists due to its ability to markedly improve the pharmaceutical properties of small-molecule drug candidates. To date, however, there remains no general means to accomplish the analogous deoxygenative trifluoromethylation of alcohols. We report herein a copper metallaphotoredox-mediated direct deoxytrifluoromethylation, wherein alcohol substrates are activated in situ by benzoxazolium salts for C(sp3)-CF3 bond formation.

Original languageEnglish (US)
Pages (from-to)11961-11968
Number of pages8
JournalJournal of the American Chemical Society
Volume144
Issue number27
DOIs
StatePublished - Jul 13 2022

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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