100113-88-0Relevant academic research and scientific papers
New ferrocenyl thio- and selenoether ligands. Preparation, characterization, and their palladium(II) complexes as catalysts for selective hydrogenation and grignard cross-coupling
Honeychuck, Robert V.,Okoroafor, Michael O.,Shen, Lie-Hang,Brubaker Jr., Carl H.
, p. 482 - 490 (2008/10/08)
A number of previously unknown ferrocenyl thioethers and selenoethers, (η5-C5H5)Fe(η5-C 5H3-1-CH2NMe2-2-SR) (R = Me, Et, i-Pr, i-Bu, isopentyl, and Ph), (R,S)-(η5-C5H5)Fe(η5-C 5H3-1-CH(CH3)-NMe2-2-SR) (R = Me, Et, i-Pr, Ph, and CH2Ph), (η5-C5H5)Fe(η5-C 5H3-1-CH2NMe2-2-SeR) (R = Me, Ph, and 4-chlorophenyl), (S,R)-(η5-C5H5)Fe(η5-C 5H3-1-CH(CH3)NMe2-2-SePh), (η5-C5H4SeR)2Fe (R = Me and Ph), and (η5-C5H5)Fe(η5-C 5H4SeMe), have been made from the appropriate ferrocene precursors via lithiation and reaction with RSSR or RSeSeR. The following techniques were used for characterization: 1H and 13C NMR, IR, MS, and elemental analysis. The PdCl2 complex of (η5-C5H5)Fe(η5-C 5H3-1-CH2NMe2-2-S-i-Pr) is a selective hydrogenation catalyst under homogeneous and heterogeneous conditions for the reduction of dienes to monoenes. The PdCl2 complexes of (R,S)-(η5-C5H5)Fe(η5-C 5H3-1-CH(CH3)NMe2-2-SPh) and (S,R)-(η5-C5H5)Fe(η5-C 5H3-1-CH(CH3)NMe2-2-SePh) are effective Grignard cross-coupling agents coupling 1-chloro-1-phenylethane with allylmagnesium bromide and allylmagnesium chloride in high yield. The preparation of the PdCl2 complexes of (η5-C5H4SePh)2Fe and (η5-C5H5)Fe(η5-C 5H3-1-CH2NMe2-2-SeR) (R = Me and 4-chlorophenyl) is also described. This paper presents the first transition-metal-catalyzed Grignard cross-coupling reaction that used a ferrocenyl thioether or selenoether as a ligand.
