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

W. Neil Palmer, Paul J. Chirik

Research output: Contribution to journalArticle

37 Scopus citations

Abstract

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
Volume7
Issue number9
DOIs
StatePublished - Sep 1 2017

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

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

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