Phosphonium salts and P-ylides

Selva, Maurizio; Perosa, Alvise; Noè, Marco

doi:10.1039/9781782626930-00132

Cited by 13 publications

(10 citation statements)

References 47 publications

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“…Phosphonium salts comprise a class of organic compounds that has enjoyed unwavering interest from the chemistry community for decades because of their applicability as reagents (e.g., ylide precursors), catalysts, or solvents (e.g., phosphonium ionic liquids (PILs)) in the synthesis of biologically active compounds. − …”

Section: Introductionmentioning

confidence: 99%

Synthesis of N-Protected 1-Aminoalkylphosphonium Salts from Amides, Carbamates, Lactams, or Imides

2021

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This report describes the development and optimization of the one-pot method for the synthesis of N -protected 1-aminoalkylphosphonium salts based on the three-component coupling of aldehydes and either amides, carbamates, lactams, imides, or urea in the presence of triarylphosphonium salts. The proposed strategy is very efficient and easy to carry out even on a larger scale (20 g) in any typical laboratory. Most reactions occur at temperatures between 50 and 100 °C in a short time (1–2 h) without requiring any catalyst, and simple workup procedures afford good to excellent yields. The exceptions are condensations with imides, which require much higher temperatures (150–170 °C) and longer reaction times (even 30 h). The possibility of carrying out the synthesis under solvent-free conditions (neat reactions) is also demonstrated. It is especially important for less reactive substrates (imides), and reactions required high temperature (or generally harsher conditions). Finally, we prove the developed one-pot methodology can be successfully applied for the synthesis of structurally diverse N -protected 1-aminoalkylphosphonium salts. Mechanistic studies showed the intermediate products of described couplings are 1-hydroxyalkylphosphonium salts, not N -hydroxyalkylamides, -imides, etc., as initially expected.

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Section: Introductionmentioning

confidence: 99%

Synthesis of N-Protected 1-Aminoalkylphosphonium Salts from Amides, Carbamates, Lactams, or Imides

2021

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“…The progresses of reactions were monitored by TLC and GC. 1 H, 13 Triphenylphosphine (6.55 g, 25 mmol, excess) was dissolved in DMF (30 mL) in a 50 mL roundbottom flask and magnetically stirred under reflux condition. 1,3-Dibromopropane (2.01 g, 1.01 mL, 10 mmol, d = 1.989 g/cm 3 ) was added dropwise with a 1 mL syringe.…”

Section: Methodsmentioning

confidence: 99%

“…Nowadays, the use of quaternary ammonium, phosphonium and pyridinium salts is a growing trend in various fields of organic synthesis, medicine and industries [1][2][3][4][5][6][7][8][9][10][11][12] . There are many reports on the synthesis of various types of the salts [1,13] . Negligible vapor pressure, high thermal stability, appropriate environmental aspects, miscibility with water and polar organic solvents, high viscosity, reusability, their versatility and non-toxicity are some of the interesting properties of these salts.…”

Section: Introductionmentioning

confidence: 99%

“…Thus, in this article we report the synthesis, thermal properties, structural characterization ( 1 H, 13 C, 31 P NMR, FT-IR, and DSC/TG/DTA) and DFT calculations of 1,3propanediylbis (triphenylphosphonium) peroxydisulfate as a mild, inexpensive and efficient oxidizing agent. Furthermore, we obtained specific heat capacity of the new salt and related bromide salt by DSC method.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, thermal properties, spectroscopic characterization and DFT computations of 1,3-propanediylbis (triphenylphosphonium) peroxydisulfate as a new oxidative agent

2020

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Thermal properties and spectroscopic characterization of new synthesized 1,3-propanediylbis (triphenylphosphonium) peroxydisulfate as a member of phosphonium persulfates were studied. 1 H, 13 C, 31 P NMR and FT-IR were used for structural characterization of the title salt. To study the thermal behavior of the salt DSC, TG and DTA methods were used. Self-accelerating decomposition temperature of anion determined 200-205 • C and decomposition point for organic moiety was recorded 340 • C by DSC method. The specific heat capacity of the salt was determined 1.32 to 1.96 j/g • C in comparison of sapphire disk between 30 to 160 • C. Theoretical DFT computations such as structural optimization, energy, charge distribution, HOMO-LUMO energy levels and thermochemical parameters were performed with the Gaussian 09 package software using B3LYP/6-31+G * level of theory. Theoretical calculations show HOMO-LUMO energy gap is 3.73 eV. Oxidation of several benzylic alcohols was performed by the persulfate salt in the water as a mild oxidative agent under reflux condition.

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“…To create new bioregulators, chemists use usual ly diverse chemical modifications of the initial structures by various pharmacophoric groups. One of these groups is the lipophilic triphenyl-phosphonium (TPP) ion [30][31][32]. Indeed, the derivatives, bearing quaternary phosphonium salts were reported to show high antimicrobial activities [33][34][35] so that these cations were considered as a new generation of effective antiseptics.…”

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confidence: 99%

1,3-Oxazol-4-ylphosphonium salts as new non-peptide inhibitors of furin

Osadchuk¹,

Kibirev²,

Shybyryn³

2019

Ukr.Biochem.J

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a series of novel triphenylphosphonium derivatives of 1,3-oxazole containing at c2 and c5-positions electron withdrawing or electron-donating groups were synthesized and characterized by 1 h, 31 P Nmr and Ir spectroscopy, element analysis and chromato-mass spectrometry. These compounds were found to be a new class of non-peptide inhibitors of furin. depending on the chemical structure, they inactivated enzyme at micromolar level by mechanism of competitive, non-competitive or mixed inhibition. evaluation of the synthesized derivatives as furin inhibitors showed that among the triphenylphosphonium salts studied by us, oxazole 12 containing 2,4-dichlorophenyl-in the c2-position and meS-group at c5 is the most active (k i = 1.57 μm) competitive inhibitor of furin. our results provided evidence that chemical modification of 1,3-oxazole-4-yltriphenylphosphonium salts may be useful for developing new more potent and selective inhibitors of furin. k e y w o r d s: furin, inhibitors, 1,3-oxazole derivatives, triphenylphosphonium salts, mechanism of inhibition.

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Phosphonium salts and P-ylides

Cited by 13 publications

References 47 publications

Synthesis of N-Protected 1-Aminoalkylphosphonium Salts from Amides, Carbamates, Lactams, or Imides

Synthesis of N-Protected 1-Aminoalkylphosphonium Salts from Amides, Carbamates, Lactams, or Imides

Synthesis, thermal properties, spectroscopic characterization and DFT computations of 1,3-propanediylbis (triphenylphosphonium) peroxydisulfate as a new oxidative agent

1,3-Oxazol-4-ylphosphonium salts as new non-peptide inhibitors of furin

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