Cobalt-Catalyzed Stereoretentive Hydrogen Isotope Exchange of C(sp3)-H Bonds

W. Neil Palmer, Paul J. Chirik

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Cobalt dialkyl complexes bearing α-diimine ligands proved to be active precatalysts for the nondirected, C(sp3)-H selective hydrogen isotope exchange (HIE) of alkylarenes using D2 gas as the deuterium source. Alkylarenes with a variety of substitution patterns and heteroatom substituents on the arene ring were successfully labeled, enabling high levels of incorporation into primary, secondary, and tertiary benzylic C(sp3)-H bonds. In some cases, the HIE proceeded with high diastereoselectivity and application of the cobalt-catalyzed method to enantioenriched substrates with benzylic stereocenters provided enantioretentive hydrogen isotope exchange at tertiary carbons.

Original languageEnglish (US)
Pages (from-to)5674-5678
Number of pages5
JournalACS Catalysis
Issue number9
StatePublished - Sep 1 2017

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • Catalysis


  • C-H activation
  • cobalt
  • deuterium
  • hydrogen isotope exchange
  • isotopic labeling
  • α-diimine


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