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

(2013) ORGANOMETALLICS. 32(21). p.6265-6270
Author
Organization
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.
Keywords
N-HETEROCYCLIC CARBENE, CROSS-COUPLING REACTIONS, ARYL CHLORIDES, BOND FORMATION, C-N, NOBEL LECTURE, IPR-ASTERISK, PRE-CATALYST, NICKEL, AMINATION

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Chicago
Martin, Anthony R, Yusuke Makida, Sebastien Meiries, Alexandra MZ Slawin, and Steven Nolan. 2013. “Enhanced Activity of [Ni(NHC)CpCl] Complexes in Arylamination Catalysis.” Organometallics 32 (21): 6265–6270.
APA
Martin, A. R., Makida, Y., Meiries, S., Slawin, A. M., & Nolan, S. (2013). Enhanced activity of [Ni(NHC)CpCl] complexes in arylamination catalysis. ORGANOMETALLICS, 32(21), 6265–6270.
Vancouver
1.
Martin AR, Makida Y, Meiries S, Slawin AM, Nolan S. Enhanced activity of [Ni(NHC)CpCl] complexes in arylamination catalysis. ORGANOMETALLICS. 2013;32(21):6265–70.
MLA
Martin, Anthony R et al. “Enhanced Activity of [Ni(NHC)CpCl] Complexes in Arylamination Catalysis.” ORGANOMETALLICS 32.21 (2013): 6265–6270. Print.
@article{8168623,
  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.},
  author       = {Martin, Anthony R and Makida, Yusuke and Meiries, Sebastien and Slawin, Alexandra MZ and Nolan, Steven},
  issn         = {0276-7333},
  journal      = {ORGANOMETALLICS},
  keywords     = {N-HETEROCYCLIC CARBENE,CROSS-COUPLING REACTIONS,ARYL CHLORIDES,BOND FORMATION,C-N,NOBEL LECTURE,IPR-ASTERISK,PRE-CATALYST,NICKEL,AMINATION},
  language     = {eng},
  number       = {21},
  pages        = {6265--6270},
  title        = {Enhanced activity of [Ni(NHC)CpCl] complexes in arylamination catalysis},
  url          = {http://dx.doi.org/10.1021/om4004863},
  volume       = {32},
  year         = {2013},
}

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