1,2-Bis[bis(pentafluorophenyl)phosphino]ethane: synthesis, characterization, and some comparisons to 1,2-bis(diphenylphosphino)ethane

Electron-Poor Olefin Polymerization Catalysts Based on Semi-Fluorinated Bis(phosphane)s

“…These signals are situated upfield from the resonance reported for the unsubstituted P,PЈ- (1,2-ethanediyl)bis(diphenylphosphane) (δ ϭ Ϫ12.5), [20] whereas in the case of 3d a 31 P chemical shift of δ ϭ Ϫ44.5 is observed. [7] This reflects the partial fluorination of the phenyl substituents in compounds 3a,b and further suggests that they may also form electron-poor complexes, although this effect should be less pronounced than in the case of 3d. …”

“…[4,5] Recently, bis(phosphane)s (R f ) 2 P(CH 2 ) 2 P(R f ) 2 (R f may be, for instance, pentafluorophenyl-or perfluoroalkyl-) have attracted attention as a new class of chelating ligands. [6,7] The electron-withdrawing character of the fluorine substituents strongly alters the electronic behaviour of the phosphorus atoms, leading to ligands that show weak σ-donor characteristics, but a high level of π-acceptor capacity. Consequently, bis(phosphane)s of this type form electron-poor transition metal complexes, e.g.…”

Neutral and ionic platinum compounds containing a cyclometallated chiral primary amine: synthesis, antitumor activity, DNA interaction and topoisomerase I–cathepsin B inhibition

“…30 As shown in Scheme 1, the same synthetic strategies were used in this work to expand the family of 1-(1-naphthyl)ethylamine derivatives including neutral complexes [PtCl{(R)-NH 2 CH(CH 3 )C 10 H 6 }{P(4-FC 6 H 4 ) 3 }] (3-R) and [PtCl{(R)-NH 2 CH-(CH 3 )C 10 H 6 }{P(CH 2 ) 3 N 3 (CH 2 ) 3 )}] (4-R), as well as the ionic compound [Pt{(R)-NH 2 CH(CH 3 )C 10 H 6 }{(C 6 F 5 ) 2 PCH 2 CH 2 P(C 6 F 5 ) 2 }]Cl (6-R). 35 On the other hand, the water-soluble monodentate phosphine 1,3,5-triaza-7-phosphaadamantane (PTA) in compound 4-R is a useful hydrophilic co-ligand, which may impart a pH-dependent behavior in biologically active transition metal compounds. In addition, introduction of fluorinated groups would permit the use of 19 F NMR spectroscopy in the characterization of the compounds.…”

Fluoroarylphosphines as ligands

“…These reagents are nucleophilic and readily react with electrophilic phosphorus reagents, in particular phosphorus mono-, di-and tri-halides. Typically diethyl ether or THF is used as solvent, and low temperatures P(C 6 F 5 ) 3 y A [1,16] (C 6 F 5 ) 2 PCH 2 P(C 6 F 5 ) 2 (dfppm) y A [17,18] PhP(C 6 F 5 )C 6 H 4 SMe-2 A [6] (C 6 F 5 ) 2 PCH 2 CH 2 P(C 6 F 5 ) 2 (dfppe) y A [19,20] Ph 2 P(h 6 -C 6 F 5 )Cr(h 6 -C 6 H 6 ) A [7,8] (C 6 F 5 )PhPCH 2 CH 2 PPh(C 6 F 5 ) A [21] A [9] (C 6 F 5 ) 2 B [53] are used for reactions involving lithium reagents. A polymersupported halodiphosphine, prepared by treating Merrifield's resin with tert-butylamine and 1,2-bis(dichlorophosphino)ethane, has allowed the synthesis of asymmetrically substituted diphosphines, such as (C 6 H 3 F 2 ) 2 PCH 2 CH 2 PPh-(C 6 H 3 F 2 ), in moderate to high yields (Scheme 2) [65].…”

“…Lability is significantly lower for chelating fluoroarylphosphines, even those with large cone angles and that are highly fluorinated, such as dfppe [19].…”