Palladium catalyzed P–C coupling – a powerful tool for the syntheses of hydrophilic phosphines

Herd, Oliver; Heßler, Antonella; Hingst, Martin; Machnitzki, Peter; Tepper, Michael; Stelzer, O.

doi:10.1016/s0920-5861(98)00123-0

Cited by 92 publications

(51 citation statements)

References 19 publications

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“…A general synthesis of R 00 R 0 RP-Au-Cl described previously [21] was used to synthesize all of the (trialkylphosphine)gold(I)chloride complexes unless otherwise specified. Modified procedures from the literature were used to synthesize the phosphine ligands [30,32] and complexes [5,21,31]. The yields of complexes reported in the Section 2 are overall yields based on the amount of gold used in each reaction.…”

Section: Resultsmentioning

confidence: 99%

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Tuning the Au(I)-mediated inhibition of cathepsin B through ligand substitutions

Gunatilleke

Barrios

2008

Journal of Inorganic Biochemistry

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Section: Resultsmentioning

confidence: 99%

“…The P(p-C 6 H 4 NH 2 )(C 6 H 5 ) 2 ligand was synthesized following a modified literature method [30]. The reaction was carried out under a nitrogen atmosphere.…”

Section: 25mentioning

confidence: 99%

Tuning the Au(I)-mediated inhibition of cathepsin B through ligand substitutions

Gunatilleke

Barrios

2008

Journal of Inorganic Biochemistry

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“…For this purpose, phosphane 3 [29] was prepared by the reaction of phosphane 1 with 4-fluorobenzoyl chloride (2) under basic conditions [44,45]. The reaction is shown in Scheme 1.…”

Section: Synthesis and X-ray Determinationmentioning

confidence: 99%

Structural and Kinetic Considerations for the Application of the Traceless Staudinger Ligation to Future ¹⁸F Radiolabeling Using XRD and ¹⁹F NMR

Köckerling

Mamat

2017

Int J of Chemical Kinetics

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A 4-fluorobenzoate-functionalized phosphane was synthesized and reacted with different azides using the traceless Staudinger ligation as a representative sample reaction for future radiolabeling purposes with short-lived radionuclides like fluorine-18. For this purpose, the reaction rate was evaluated at different temperatures. The effect of starting material concentrations and the influence of the steric effect coming from the applied azides were investigated. 19 F NMR was used to determine the reaction half-live (τ 1/2 ) and the reaction rate constant (k obs ) of this ligation under mild reaction conditions in a water-acetonitrile mixture. Furthermore, the phosphane key compound 1 (orthorhombic, space group Pna2 1 , a = 18.6363(9), b = 8.3589(4), c = 18.5480(9)Å, V = 2889.4(2)Å 3 , Z = 8, D obs = 1.277 g/cm 3 ), which acts as starting material for all subsequent syntheses, and the fluorine-containing phosphane 3 (monoclinic, space group P2 1 /c, a = 8.321(2), b = 16.160(4), c = 14.940(4)Å, β = 99.51(1)°, V = 1981.4(8)Å 3 , Z = 4, D obs = 1.342 g/cm 3 ) were analyzed by single-crystal XRD.

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“…77,164 With weakly electrophilic acetylenes, addition of secondary phosphines requires strong bases or high temperature to proceed.…”

Section: Scheme 22mentioning

confidence: 99%

Nucleophilic and free-radical additions of phosphines and phosphine chalcogenides to alkenes and alkynes

Arbuzova¹,

Гусарова²,

Трофимов³

2006

Arkivoc

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Palladium catalyzed P–C coupling – a powerful tool for the syntheses of hydrophilic phosphines

Cited by 92 publications

References 19 publications

Tuning the Au(I)-mediated inhibition of cathepsin B through ligand substitutions

Tuning the Au(I)-mediated inhibition of cathepsin B through ligand substitutions

Structural and Kinetic Considerations for the Application of the Traceless Staudinger Ligation to Future ¹⁸F Radiolabeling Using XRD and ¹⁹F NMR

Nucleophilic and free-radical additions of phosphines and phosphine chalcogenides to alkenes and alkynes

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Palladium catalyzed P–C coupling – a powerful tool for the syntheses of hydrophilic phosphines

Cited by 92 publications

References 19 publications

Tuning the Au(I)-mediated inhibition of cathepsin B through ligand substitutions

Tuning the Au(I)-mediated inhibition of cathepsin B through ligand substitutions

Structural and Kinetic Considerations for the Application of the Traceless Staudinger Ligation to Future 18F Radiolabeling Using XRD and 19F NMR

Nucleophilic and free-radical additions of phosphines and phosphine chalcogenides to alkenes and alkynes

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Product

Resources

About

Structural and Kinetic Considerations for the Application of the Traceless Staudinger Ligation to Future ¹⁸F Radiolabeling Using XRD and ¹⁹F NMR