Nucleophilic additon of phosphine to 1-(tert-butyl)-4-vinylbenzene: a short-cut to bulky secondary and tertiary phosphines and their chalcogenides

Гусарова, Н. К.; Малышева, С. Ф.; Kuimov, Vladimir A.; Белогорлова, Н. А.; Mikhailenko, V. L.; Трофимов, Б. А.

doi:10.1016/j.mencom.2008.09.011

Cited by 39 publications

(8 citation statements)

References 31 publications

(3 reference statements)

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“…Tris(2-pyridyl)phosphine 1 and oxide 2 were synthesized according to procedures [6,7], sulfide 3 and selenide 4 were prepared from phosphine 1 and elemental sulfur or selene in toluene according to procedure [8]. The solvents were purified using standard procedure.…”

Section: Materials and Physical Measurementsmentioning

confidence: 99%

Dipole moments and conformational analysis of tris(2-pyridyl)phosphine and tris(2-pyridyl)phosphine chalcogenides. Experimental and theoretical study

Vereshchagina

Чачков

Alimova

et al. 2014

Journal of Molecular Structure

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Section: Materials and Physical Measurementsmentioning

confidence: 99%

Dipole moments and conformational analysis of tris(2-pyridyl)phosphine and tris(2-pyridyl)phosphine chalcogenides. Experimental and theoretical study

Vereshchagina

Чачков

Alimova

et al. 2014

Journal of Molecular Structure

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“…Here we have tried to convert the toxic PH 3 to commercially important tertiary phosphine ligand. As a phosphine source, its mixture with hydrogen generated from red phosphorus and 60%‐70%‐aqueous alkali in the separate flask has been used …”

Section: Resultsmentioning

confidence: 99%

Tri(1‐naphthyl)phosphine as a ligand in palladium‐free Sonogashira cross‐coupling of arylhalogenides with acetylenes

Govdi

Vasilevsky

Малышева

et al. 2018

Heteroatom Chemistry

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Tri(1‐naphthyl)phosphine (Np3P) has been easily prepared in 34% yield from red phosphorus and 1‐bromonaphthalene in the superbasic system t‐BuONa/DMSO. The expedient procedures for the synthesis of aryl acetylenes by Sonogashira coupling of aryl iodides with terminal alkynes using Np3P as a ligand have been developed. For the first time, it is found that the reaction with compounds containing electron‐donating substituents preferably affords buta‐1,3‐diynes.

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“…The highest activity showed a redox monomer М 2 and its polymer RP 2 . Increasing the concentration of BuOH to 109 mmol, the temperature to 70 °C in iodine alcohol solutions RP 2 and M 2 contributed to complete conversion of РН 3 forming 10-64% dialkylphosphite and 36-52% trialkylphosphate (experiments [8][9][10][11].…”

Section: Tablementioning

confidence: 99%

“…Synthesis, on the basis of PH 3 , is used very rarely and it is not realized in the industry because there are no effective technological methods of its obtaining. Trofimov with colleagues [7][8][9][10][11][12][13][14] developed in recent years convenient methods of synthesis of organophosphorus compounds on the basis of phosphine, generated in the water and organic medium from red phosphorus in the presence of the superstrong bases. Phosphin can be used for obtaining various OPhC which are important supplementary reagents, construction blocks, semi-products, and also ligands for metalcomplex catalysts, extragents and аntipyrenes.…”

Section: Introductionmentioning

confidence: 99%

The Synthesis of Organophosphorus Compounds from Phosphine and Alcohols in the Presence of Quinones and Redox Polymers on their Basis

et al. 2012

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This article presents the synthesis of phosphoric acid esters from phosphoric hydrogen РН 3 and aliphatic alcohols. The process is based on the oxidation of phosphine by quinones and redox polymers on the basis of mono-and disubstituted quinoid derivatives of monoethanolamine vinyl ether. Molecular iodine is used as a catalyst. Two-, three-, four-and multicomp onent systems are studied in order to determine optimal conditions of the oxidation of phosphine quinones and repoxpolymers on their basis. The rate and selectivity of reaction were monitored by the absorption of РН 3 . As alcohols used aliphatic alcohols: BuOH, PrOH, EtOH, MeOH. Organophosphorus compounds were analyzed by a chromatographic method. It was established that alcohol solutions of individual components of reactionary system (quinones, redox ionites or iodine) are characterized by a low activity in relation to phosphine. Organophosphorus compounds are formed in insignificant quantities. In the mixed alcohol solution of benzoquinone takes place PH 3 oxidation forming trialkylphosphates. Conversion of phosphine constitutes 80-100%. Increasing the concentration of reagents of catalytic system has a positive effect on the process as a whole. Similar patterns were obtained when redox monomers and polymers on the base of quinones in the presence of iodine were used as oxidants. Esters of phosphoric acid -dialkylphosphites and esters of phosphorous acid -trialkylphosphates were identified as organophosphorus compounds. By selecting a redox agent in a zone of the catalysis it is possible to direct process in the desirable direction. The most activity in the oxidation of phosphine by iodine-alcohol solutions of quinoid monomers and polymers, is exhibited by 2-[N-(2-vinyloxy) ethyl]amino-NQ and polymer on their basis. Results of our experiments and literature data on oxidation-reduction processes with participation of iodine and quinones in organic solutions allowed to propose the separate oxidation-reduction mechanism of formation of organophosphorus compounds. In investigated multicomponent systems, the synergetic effect is manifested which is reached at the expense of distribution of oxidation-reduction functions among iodine, quinones and its derivatives. In this report, for the first time, it is established reactionary ability of quinones and redox ionites on their basis in an oxidizing alkoxylation of phosphine to valuable esters of acids of phosphorus. Reaction can be used for purification of exhaust and technological gases from phosphine and its utilization.

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Nucleophilic additon of phosphine to 1-(tert-butyl)-4-vinylbenzene: a short-cut to bulky secondary and tertiary phosphines and their chalcogenides

Cited by 39 publications

References 31 publications

Dipole moments and conformational analysis of tris(2-pyridyl)phosphine and tris(2-pyridyl)phosphine chalcogenides. Experimental and theoretical study

Dipole moments and conformational analysis of tris(2-pyridyl)phosphine and tris(2-pyridyl)phosphine chalcogenides. Experimental and theoretical study

Tri(1‐naphthyl)phosphine as a ligand in palladium‐free Sonogashira cross‐coupling of arylhalogenides with acetylenes

The Synthesis of Organophosphorus Compounds from Phosphine and Alcohols in the Presence of Quinones and Redox Polymers on their Basis

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