Iron(I) in Negishi cross-coupling reactions

Christopher J Adams, Robin B Bedford, Emma Carter, Nicholas J Gower, Mairi F Haddow, Jeremy N Harvey, Michael Huwe, M Angeles Cartes, Stephen M Mansell, Carla Mendoza, Damien M Murphy, Emily C Neeve, Joshua Nunn

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Abstract

Herein we demonstrate both the importance of Fe(I) in Negishi cross-coupling reactions with arylzinc reagents and the isolation of catalytically competent Fe(I) intermediates. These complexes, [FeX-(dpbz)(2)] [X = 4-tolyl (7), Cl (8a), Br (8b); dpbz = 1,2-bis(diphenylphosphino)benzene], were characterized by crystallography and tested for activity in representative reactions. The complexes are low-spin with no significant spin density on the ligands. While complex 8b shows performance consistent with an on-cycle intermediate, it seems that 7 is an off-cycle species.

Original languageEnglish
Pages (from-to)10333-10336
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number25
DOIs
Publication statusPublished - 27 Jun 2012

Keywords

  • ALKYL-HALIDES
  • GRIGNARD REAGENTS
  • COMPLEXES
  • LIGAND
  • REACTIVITY
  • CATALYSIS

Cite this

Adams, C. J., Bedford, R. B., Carter, E., Gower, N. J., Haddow, M. F., Harvey, J. N., Huwe, M., Angeles Cartes, M., Mansell, S. M., Mendoza, C., Murphy, D. M., Neeve, E. C., & Nunn, J. (2012). Iron(I) in Negishi cross-coupling reactions. Journal of the American Chemical Society, 134(25), 10333-10336. https://doi.org/10.1021/ja303250t