Synthesis and structural characterization of ferrocene phosphines modified with polar pendants and their palladium(II) complexes. Part I: N-aminocarbonyl and N-acyl phosphinoferrocene carboxamides

Add time:08/28/2019    Source:sciencedirect.com

Acylation of 1′-(diphenylphosphino)-1-(aminocarbonyl)ferrocene, Ph2PfcCONH2 (1; fc = ferrocene-1,1′-diyl), afforded a series of acyl-ureas including Ph2PfcCONHCONHEt (1a), Ph2PfcCONHCONHPh (1b), and Ph2PfcCONHCONMe2 (1c) as well as the acetyl derivative Ph2PfcCONHAc (1d). Compounds 1a-d were converted to the corresponding phosphine oxides (2a-d) and further examined as ligands in Pd(II) complexes. The reactions of 1a-d with [PdCl2(cod)] (cod = cycloocta-1,5-diene) at a 2:1 ligand-to-metal ratio gave the bis(phosphine) complexes [PdCl2(L-κP)2] (3a-d; L = 1a-d), whereas the reactions with [Pd(LNC)Cl]2 (LNC = [2-(dimethylamino-κN)methyl]phenyl-κC1) produced the bridge-cleavage products, [PdCl(LNC)(L-κP)] (4a-d). Removal of the Pd-bound halide from 4a-d with Ag[SbF6] furnished the corresponding cationic bis-chelate complexes [Pd(LNC)(L-κ2O,P)][SbF6] (5a-d). All compounds were characterized by NMR and IR spectroscopy, electrospray ionization mass spectrometry, and elemental analysis. The crystal structures of 1a, 2a-c, 3a·2CHCl3, 3b·2CHCl3, 3d·2CHCl3, 4a·3CHCl3, 4b·2.5CHCl3, 5a·CHCl3, 5b·2CH2Cl2, and 5d were determined by single-crystal X-ray diffraction analysis, which revealed that the hydrogen-bonded arrays formed in the crystals of free ligands are often preserved in the structures of their complexes.

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