- Synthesis of 1,1′,2-trisubstituted aryl-based ferrocenyl phosphines as precursors for immobilized ligands
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Ferrocenylaryl or ferrocenylheteroaryl phosphines bearing a carboxaldehyde group, [Fe{1-PPh2(spacer)-2-NMe2CH2C 5H3}(C5H4CHO)] (spacer = none (rac-12), 1,4-phenylene (rac-13), 1,3-phenylene (rac-14), 2,5-thienylene (rac-15)), were prepared in a facile four-step sequence starting with dibromination of N,N-dimethylaminomethylferrocene (1) followed by Negishi cross-coupling between 1,1′-dibromo-2-N,N-dimethylaminomethylferrocene (rac-2) and aryl or heteroaryl bromide phosphine oxides, Br-spacer-P(O)Ph 2 (spacer = 1,4-phenylene, 1,3-phenylene, 2,5-thienylene), reduction with trichlorosilane, and functionalization of the 1′-position of the cyclopentadienyl ring. All products were fully characterized by spectroscopy (1H, 13C, and 31P NMR, MS, IR) and for rac-3, rac-7 and rac-11 also by X-ray crystallography. Furthermore, preliminary studies on the grafting of rac-12 on silica were conducted.
- Madalska, Martyna,Loennecke, Peter,Ivanovski, Vladimir,Hey-Hawkins, Evamarie
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p. 5852 - 5861
(2013/11/19)
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- 1,2-Disubstituted aryl-based ferrocenyl phosphines
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Ferrocenylaryl-or ferrocenylheteroarylphosphines [Fe{1-PPh 2(spacer)-2-NMe2CH2C5H 3}(C5H5)] (spacer = 1,4-phenylene (rac-6), 1,3-phenylene (rac-7), 4,4′-biphenylene (rac-8), 2,5-thienylene (rac-9)) were prepared in a facile two-step sequence starting with Negishi cross-coupling between N,N-dimethylaminomethylferrocene and aryl halide phosphine oxides, Br-spacer-P(O)Ph2, followed by reduction with trichlorosilane. All products were characterized spectroscopically (1H, 13C, and 31P NMR, MS, FTIR), and rac-6, the corresponding phosphine oxide rac-2, and rac-9 were also characterized by X-ray crystallography. Furthermore, the redox properties of rac-2-9 were studied by cyclic voltammetry.
- Madalska, Martyna,Loennecke, Peter,Hey-Hawkins, Evamarie
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p. 2019 - 2025
(2013/05/08)
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