Deuteration of Formyl Groups via a Catalytic Radical H/D Exchange Approach

Yueteng Zhang, Peng Ji, Yue Dong, Yongyi Wei, Wei Wang

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

H/D exchange at formyl groups represents the straightforward approach to C-1 deuterated aldehydes. This transformation has been recently realized by transition metal and NHC carbene catalysis. Mechanistically, all of these processes involve an ionic pathway. Herein, we report a distinct photoredox catalytic, visible light mediated neutral radical approach. Selective control of highly reactive acyl radical in the energy barrier surmountable, reversible reaction enables driving the formation of deuterated products when an excess of D2O is employed. The power of the H/D exchange process has been demonstrated for not only aromatic aldehydes but also aliphatic substrates, which have been difficult in transitional metal catalyzed H/D exchange reactions, and for selective late-stage deuterium incorporation into complex structures with uniformly high deuteration level (>90%).

Original languageEnglish (US)
Pages (from-to)2226-2230
Number of pages5
JournalACS Catalysis
Volume10
Issue number3
DOIs
StatePublished - Feb 7 2020

Keywords

  • aldehyde
  • deuteration
  • H/D exchange
  • photoredox
  • radical reaction

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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