Enhanced activity of [Ni(NHC)CpCl] complexes in arylamination catalysis

Anthony R. Martin, Yusuke Makida, Sébastien Meiries, Alexandra M.Z. Slawin, Steven P. Nolan

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Abstract

Seven new air- and moisture-stable nickel complexes bearing flexible bulky NHC (N-heterocyclic carbene) ancillary ligands (NHC = IPr, IPrTol, IPrOMe, IPent) are reported. Using experimentally determined crystal structures, the steric environments of [Ni(NHC)CpCl] complexes were analyzed. A survey of their catalytic activity in Buchwald-Hartwig arylamination has been performed. In comparison to less sterically demanding analogues (NHC = IMes, SIMes, IPr, SIPr), an increase in the ligand bulkiness was found to correlate to a dramatic enhancement of the C-N bond formation efficiency. Finally, the catalytic activity of the most active precatalyst, [Ni(IPrOMe)CpCl], was further explored and the scope and limitations of this complex were examined.

Original languageEnglish
Pages (from-to)6265-6270
Number of pages6
JournalOrganometallics
Volume32
Issue number21
DOIs
Publication statusPublished - Nov 11 2013

All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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    Martin, A. R., Makida, Y., Meiries, S., Slawin, A. M. Z., & Nolan, S. P. (2013). Enhanced activity of [Ni(NHC)CpCl] complexes in arylamination catalysis. Organometallics, 32(21), 6265-6270. https://doi.org/10.1021/om4004863