Base-Mediated Remote Deuteration of N-Heteroarenes – Broad Scope and Mechanism

Sara Kopf, Jiali Liu, Robert Franke, Haijun Jiao, Helfried Neumann, Matthias Beller

Research output: Contribution to journalArticlepeer-review

5 Scopus citations

Abstract

Deuterated organic molecules provide the basis for many applications in life sciences and material research. Thus, methodologies to access labeled compounds with defined selectivity continue to be important. Using KOtBu as base and DMSO-d6 as deuterium source, we present a general and applicable method for the selective deuteration of a set of nitrogen-containing heterocycles (pyridines, azines and bioactive molecules). Experimental and DFT mechanistic studies indicate that this reaction proceeds via deprotonation of the substrates by the dimsyl anion. The relative thermodynamic stability of the heterocycle anions determines the distribution and degree of deuteration.

Original languageEnglish
Article numbere202200204
JournalEuropean Journal of Organic Chemistry
Volume2022
Issue number19
DOIs
StatePublished - 19 May 2022
Externally publishedYes

Keywords

  • Density functional calculations
  • Deuterium
  • Heterocycles
  • Hydrogen isotope exchange
  • Isotopic labeling

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