Mesoionic Carbene (MIC)-Catalyzed H/D Exchange at Formyl Groups

Wei Liu, Liang Liang Zhao, Mohand Melaimi, Lei Cao, Xingyu Xu, Jean Bouffard, Guy Bertrand, Xiaoyu Yan

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

H/D exchange at formyl groups is the most direct approach for the synthesis of deuterated aldehydes. Platinum-group metal complexes have been employed to catalyze this transformation, with significant substrate scope limitations. Although N-heterocyclic carbenes can also activate the C–H bond of aldehydes through the formation of Breslow intermediates, benzoin condensation and other C–C-bond-forming pathways have so far outpaced synthetically useful H/D exchange. Investigation of the reaction of aldehydes with 1,2,3-triazolylidenes has revealed the reversible formation of Breslow intermediates and the inhibition of the condensation steps in methanol solvent. 1,2,3-Triazolylidenes catalyze the H/D exchange of aryl, alkenyl, and alkyl aldehydes in high yields and deuterium incorporation levels using deuterated methanol as an affordable D source. The unique properties of these mesoionic carbenes (MICs) enable a streamlined preparation of deuterated synthetic intermediates and pharmacophores that are highly valuable as mechanistic and metabolic probes.

Original languageEnglish
Pages (from-to)2484-2494
Number of pages11
JournalChem
Volume5
Issue number9
DOIs
StatePublished - 12 Sep 2019

Keywords

  • Breslow intermediate
  • N-heterocyclic carbenes
  • SDG3: Good health and well-being
  • isotope exchange
  • mesoionic carbenes
  • organocatalysis

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