Redox Activity of Pyridine-Oxazoline Ligands in the Stabilization of Low-Valent Organonickel Radical Complexes

Clifton L. Wagner, Gabriel Herrera, Qiao Lin, Chunhua T. Hu, Tianning Diao

Research output: Contribution to journalArticlepeer-review

Abstract

Low-valent organonickel radical complexes are common intermediates in cross-coupling reactions and metalloenzyme-mediated processes. The electronic structures of N-ligand supported nickel complexes appear to vary depending on the actor ligands and the coordination number. The reduction products of a series of divalent (pyrox)Ni complexes establish the redox activity of pyrox in stabilizing electron-rich Ni(II)-alkyl and -aryl complexes by adopting a ligand-centered radical configuration. The reduced pyrox imparts an enhanced trans-influence. In contrast, such redox activity was not observed in a (pyrox)Ni(I)-bromide species. The excellent capability of pyrox in stabilizing electron-rich Ni species resonates with its proclivity in promoting the reductive activation of C(sp3) electrophiles in cross-coupling reactions.

Original languageEnglish (US)
Pages (from-to)5295-5300
Number of pages6
JournalJournal of the American Chemical Society
Volume143
Issue number14
DOIs
StatePublished - Apr 14 2021

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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