Water soluble phosphines

Brauer, David J.; Hingst, Martin; Kottsieper, Konstantin W.; Liek, Christian; Nickel, Thomas; Tepper, Michael; Stelzer, O.; Sheldrick, William S.

doi:10.1016/s0022-328x(01)01371-7

Cited by 78 publications

(54 citation statements)

References 61 publications

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“…The importance of water-soluble phosphines is arising day-after-day. Efficient watersoluble ligands can be obtained by linking it to an appropriate hydrophilic group [3,4]. This group may be cationic (e.g., − [4].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of bis(diphenylphosphinomethyl)amino ligands and their Ni(II), Pd(II) complexes: Application to hydrogenation of styrene

Keleş

Altan

Serindağ

2008

Heteroatom Chemistry

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Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of bis(diphenylphosphinomethyl)amino ligands and their Ni(II), Pd(II) complexes: Application to hydrogenation of styrene

Keleş

Altan

Serindağ

2008

Heteroatom Chemistry

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“…The observed chemical shifts revealed further that 4 and 7 had been transformed into new products. Samples containing 4 displayed a single sharp line at 61.0 (in CH 2 Cl 2 /Et 3 N) or 56.8 ppm (in dmf/Et 3 N) which we assigned, on the basis of the similarity with the data of analogous compounds, [19] to the bis(chelate) complex 8. This hypothesis is further corroborated by the finding that formation of the same product was likewise observed upon treatment of a solution of 4 with excess triethylamine (Scheme 3).…”

Section: Resultsmentioning

confidence: 74%

“…Characterisation of the novel complex 7 by solution NMR spectroscopy reveals, as in the case of 4, [10] the presence of a mixture of cis and trans isomers, which can be easily distinguished by their characteristic 31 P NMR spectroscopic data [10,11,19] [δ( 31 P) = 33.3 ppm (cis isomer), 20.3 ppm (trans isomer), isomer ratio approx. 1:3 by integration].…”

Section: Resultsmentioning

confidence: 99%

On the Immobilisation of Catechol Phosphane Palladium Complexes on Titania

2008

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Two isomeric bis(phosphane) palladium chloride complexes with functional catechol phosphane ligands were immobilised on different specimens of TiO 2 . The solid materials were characterised by 31 P NMR spectroscopy both when dry and as suspensions in various solvents. The NMR spectroscopic studies demonstrated that the resistance towards leaching varies strongly with the nature of the carrier material and

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“…It was previously reported that the aromatic functionally substituted tertiary phosphines are successfully prepared by cross coupling of bromo(iodo)arenes III with diphenyl(trimethylsilyl)phosphine [3] and even with diphenylphosphine [4,5], whereas tertiary phosphines with bulky alkyl groups and functional groups in the aromatic ring were not obtained.…”

Section: äääääääääääämentioning

confidence: 99%

Synthesis of Sterically Hindered Secondary and Tertiary Alkyl(Aryl)Phosphines

2005

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Cross coupling of silylphosphines with 2-halobenzenecarboxylates or 2-halophenyl ethers, catalyzed with zero-valent palladium complexes can not be used as a procedure for preparing sterically hindered tertiary phosphines. The latter compounds can be successfully prepared by means of phosphorylation of corresponding o-lithiated derivatives.In [1], a procedure for preparing secondary alkyl-(aryl)phosphines of the general formula RArPH containing electron-donor and electron-acceptor substituents in the aromatic ring have been proposed. This procedure is based on cross coupling of alkyl-(trimethylsilyl)phosphines with corresponding aryl halides in the presence of catalytic amounts of zerovalent palladium.In this work we have studied the cross coupling of trimethylsilyl derivatives of secondary phosphines R 1 R 2 PSiMe 3 Ia and Ib [R 1 = i-Pr, R 3 = tert-Bu (a); R 1 = tert-Bu, R 2 = Ph (b)] and also of bis-silylated primary phosphines RP(SiMe 3 ) 2 IIa and IIb [R = i-Pr ÄÄÄÄÄÄÄÄÄÄÄÄ (a); R = tert-Bu (b)] with various aryl halides YC 6 H 4 Hlg III [reactions (1) and (2)] with the purpose to establish the utility of the above procedure for preparing tertiary alkyl(aryl)phosphines R 1 R 2 PC 6 H 4 Y IV and RP(C 6 H 4 Y) 2 V with secondary and tertiary alkyl groups and a series of o-and m-substituents in the aromatic ring. Bulky radicals in phosphines IV and V, including o-substituted in the aromatic ring, were chosen to impart configurational stability to racemic tertiary phosphines which we proposed to resolve into optical antipodes [2]. Substituents containing alkoxycarbonyl groups were introduced to render the synthesized phosphine ligands water-soluble after hydrolysis. R 1 R 2 PSiMe 3 + 4 c = Y Hlg 7777776 3Me 3 SiHlg 235 mol% Pd(0), to 4 c = Y PR 1 R 2 I III IV R(PSiMe 3 ) 2 + 2III 7777776 3Me 3 SiHlg 235 mol% Pd(0), to 4 c = Y PR 2 V II (1) (2) ÄÄÄÄÄÄÄÄÄÄÄÄIt was previously reported that the aromatic functionally substituted tertiary phosphines are successfully prepared by cross coupling of bromo(iodo)arenes III with diphenyl(trimethylsilyl)phosphine [3] and even with diphenylphosphine [4,5], whereas tertiary phosphines with bulky alkyl groups and functional groups in the aromatic ring were not obtained.Preliminary experiments showed [1] that the synthesis of tertiary phosphines by reaction (2) requires much more rigid conditions (1303140oC) than the synthesis of secondary phosphines (503100oC), and the slowest reactions are observed with o-substituted haloarenes III. In view of these results, we primarily studied the cross coupling of bis-silylphosphines IIa and IIb with bromide IIIa (Y = 3-CF 3 ) which was expected to be the most resistant to bromo-and especially iodotrimethylsilane evolved upon prolonged heating of the components of reaction (2). Reactions (1) and (2) were carried out in sealed ampules with

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Water soluble phosphines

Cited by 78 publications

References 61 publications

Synthesis and characterization of bis(diphenylphosphinomethyl)amino ligands and their Ni(II), Pd(II) complexes: Application to hydrogenation of styrene

Synthesis and characterization of bis(diphenylphosphinomethyl)amino ligands and their Ni(II), Pd(II) complexes: Application to hydrogenation of styrene

On the Immobilisation of Catechol Phosphane Palladium Complexes on Titania

Synthesis of Sterically Hindered Secondary and Tertiary Alkyl(Aryl)Phosphines

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