Abstract
The treatment of 4,5-dimethyl-1,3-bis(2-pyridylmethyl)-1H-imidazolium chloride with M[N(SiMe3)2]2(THF)2 (M = Ca, Yb) in 1:2 molar ratio results in the formation of a carbene fragment, activation of the picolyl CH bond, and dearomatization of one of the pyridine rings and affords bis(amido) complexes [(NHC)MN(SiMe3)2]2 (M = Ca (2), Yb (3)) coordinated by a μ2-bridging pincer NHC amido ligand. Complexes 2 and 3 demonstrate high catalytic activity and excellent regio- and chemoselectivities in the intermolecular hydrophosphination of styrene with both primary and secondary phosphines. Complexes 2 and 3 enable selective addition of PhPH2, Ph2PH, (CH2)4NH, and (CH2)5NH to para-divinylbenzene with high conversions under mild conditions. Tandem hydrophosphination/hydroamination of para-divinylbenzene was also performed.
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