J. Albert, Lucía D'Andrea, J. Granell
Jun 15, 2007
Citations
0
Influential Citations
26
Citations
Journal
Journal of Organometallic Chemistry
Abstract
Abstract ( R )-1-Phenylethyl-benzylidene-amine ( 1 ) reacted with Pd(OAc) 2 in acetic acid at 60 °C under nitrogen affording the acetato-bridged dinuclear endo five-membered ortho -cyclopalladated compound (μ-OAc) 2 [Pd(κ 2 - C , N -( R )-C 6 H 4 -CH N-CHMe-Ph)] 2 ( 2 ) in 65% yield. Compound 2 was converted by a metathesis reaction with LiCl into the corresponding chloro-bridged dinuclear cyclopalladated compound (μ-Cl) 2 [Pd(κ 2 - C , N -( R )-C 6 H 4 -CH N-CHMe-Ph)] 2 ( 3 ). 1 H NMR of CDCl 3 solutions of compounds 2 and 3 treated separately with py- d 5 , ( R )-1-phenylethylamine and racemic 1-phenylethylamine were consistent with the endo cyclopalladated structure and the R absolute configuration of the chiral carbon atoms of compounds 2 and 3 . Compounds 2 and 3 reacted with carbon monoxide in methanol affording, as major compounds, methyl 2-formylbenzoate (91% chemical yield) and the epimers of 3-methoxy-2-[( R )-1-phenylethyl]isoindolin-1-one (64% chemical yield) in ca. 20% diastereomeric excess, respectively. The trans isomer of compound 3 crystallized in the P 2 1 monoclinic space group with a = 10.430(4) A, b = 12.082(8) A, c = 11.168(4) A and β = 95.20(3)° and presented C–H⋯Cl intramolecular and C–H⋯Pd intermolecular non-conventional hydrogen bonds.