Enhanced Activity of [Ni(NHC)CpCl] Complexes in Arylamination Catalysis

Anthony Martin; Yusuke Makida; Sebastien Michel Bernard Meiries; Alexandra Martha Zoya Slawin; Steven Patrick Nolan

doi:10.1021/om4004863

Enhanced Activity of [Ni(NHC)CpCl] Complexes in Arylamination Catalysis

Anthony Martin, Yusuke Makida, Sebastien Michel Bernard Meiries, Alexandra Martha Zoya Slawin, Steven Patrick Nolan

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

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
Early online date	7 Oct 2013
DOIs	https://doi.org/10.1021/om4004863
Publication status	Published - 11 Nov 2013

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title = "Enhanced Activity of [Ni(NHC)CpCl] Complexes in Arylamination Catalysis",

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.",

author = "Anthony Martin and Yusuke Makida and Meiries, {Sebastien Michel Bernard} and Slawin, {Alexandra Martha Zoya} and Nolan, {Steven Patrick}",

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doi = "10.1021/om4004863",

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T1 - Enhanced Activity of [Ni(NHC)CpCl] Complexes in Arylamination Catalysis

AU - Martin, Anthony

AU - Makida, Yusuke

AU - Meiries, Sebastien Michel Bernard

AU - Slawin, Alexandra Martha Zoya

AU - Nolan, Steven Patrick

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*, 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.

AB - 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.

U2 - 10.1021/om4004863

DO - 10.1021/om4004863

M3 - Article

SN - 0276-7333

VL - 32

SP - 6265

EP - 6270

JO - Organometallics

JF - Organometallics

IS - 21

ER -

Enhanced Activity of [Ni(NHC)CpCl] Complexes in Arylamination Catalysis

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