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

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

doi:10.1021/om4004863

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

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

Research output: Contribution to journal › Article › peer-review

90 Citations (Scopus)

Abstract

Seven new air- and moisture-stable nickel complexes bearing flexible bulky NHC (N-heterocyclic carbene) ancillary ligands (NHC = IPr, IPr^Tol, IPr^OMe, 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(IPr^OMe)CpCl], was further explored and the scope and limitations of this complex were examined.

Original language	English
Pages (from-to)	6265-6270
Number of pages	6
Journal	Organometallics
Volume	32
Issue number	21
DOIs	https://doi.org/10.1021/om4004863
Publication status	Published - Nov 11 2013
Externally published	Yes

All Science Journal Classification (ASJC) codes

Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1021/om4004863

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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.",

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T1 - Enhanced activity of [Ni(NHC)CpCl] complexes in arylamination catalysis

AU - Martin, Anthony R.

AU - Makida, Yusuke

AU - Meiries, Sébastien

AU - Slawin, Alexandra M.Z.

AU - Nolan, Steven P.

PY - 2013/11/11

Y1 - 2013/11/11

N2 - 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.

AB - 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.

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

Abstract

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