TY - JOUR
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.
UR - https://www.scopus.com/pages/publications/84887709395
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 -