Abstract
Tetra-ether substituted imidazolium salts, LHX (where LH = N, N′-bis(2,2-diethoxyethyl)imidazolium cation and X = Br, BF 4, PF 6, BPh 4, NO 3 and NTf 2 anions) were derived from imidazole. Attempts to produce aldehyde functionalized imidazolium salt through acid hydrolysis of LHBr resulted an unexpected tetra-hydroxy compound L AHBr and the dialdehyde compound L BHBr. Reaction of LHBr with Ag 2O afforded [L 2Ag][AgBr 2] ( 1). Mononuclear Pd-complex trans-[L 2PdCl 2] ( 2) and dinuclear Pd-complex [(LPdCl 2) 2] ( 3) were obtained by 1:1 and 1:2 reaction of in situ generated Ag-carbene with Pd(CH 3CN) 2Cl 2. cis-[LPdPPh 3Cl 2] ( 4) was synthesized from reaction of PPh 3 with dinuclear complex 3. Hydrolysis of 3 under acidic conditions also generates a hydroxy derivative 3A and the aldehyde derivative 3B. Direct heating of LHBr with Ni(OAc) 2 · 4H 2O at 120 °C under vacuum generated trans-[L 2NiBr 2] ( 5). These complexes were characterized by NMR, mass, elemental analysis, and X-ray single crystal diffraction analysis. Pd--Pd interaction was observed in 3. All the Pd complexes exhibited excellent catalytic activity in Heck reaction.
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