One-pot synthesis of ultra-branched mixed tetradentate tripodal phosphines and phosphine chalcogenides

Гусарова, Н. К.; Kuimov, Vladimir A.; Малышева, С. Ф.; Белогорлова, Н. А.; Albanov, A. I.; Трофимов, Б. А.

doi:10.1016/j.tet.2012.08.091

Cited by 12 publications

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“…This fact is in contradiction with the aforementioned literature data [2], but it is in accordance with the commonly accepted notions of a relatively low reactivity of secondary phosphine oxides in the reactions of radical addition to the double bond [3,[17][18][19].…”

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confidence: 59%

“…Reactions of this type have been successfully realized under radical conditions by the example of divinyl [1], diallyl [2,3], trivinyl [4], tetravinyl [5] ethers, divinyl chalcogenides [6][7][8][9], as well as tris(4-vinylbenzyl)phosphine oxide [10]. As a result, promising polydentate ligands for metal complexes, including metallacrown ethers [1,[11][12][13] have been synthesized.…”

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confidence: 99%

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Reaction of secondary phosphine chalcogenides with diallylamine

et al. 2014

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Diphenyl-or bis(2-phenylethyl)phosphine sulfides and -phosphine selenides react with diallylamine under radical initiation (UV or AIBN) to afford the corresponding diadducts and tetrahydropyrrolylmethyl phosphine chalcogenides. The yield and the ratio of the products depend on the structure of the starting secondary phosphine chalcogenides.Addition of secondary phosphines and phosphine chalcogenides to polyalkenes is a convenient atomeconomic approach to the synthesis of polyphosphines and polyphosphine chalcogenides including their functional derivatives. Reactions of this type have been successfully realized under radical conditions by the example of divinyl [1], diallyl [2, 3], trivinyl [4], tetravinyl [5] ethers, divinyl chalcogenides [6-9], as well as tris(4-vinylbenzyl)phosphine oxide [10]. As a result, promising polydentate ligands for metal complexes, including metallacrown ethers [1, 11-13] have been synthesized.At the same time, there are no data in the literature on the reaction of diallylamine with secondary phosphine chalcogenides, although substituted diallylamines react with diphenylphosphine oxide (AIBNinitiation) [2] and diphenylphosphine sulfide (microwave activation) [3] to give cyclic adducts, phosphoruscontaining pyrrolidines (Scheme 1).In the present work we have studied for the first time the radical addition of secondary phosphine sulfides and phosphine selenides to diallylamine in order to develop a general convenient atom-economic method of the synthesis of functional tertiary phosphine chalcogenides containing an amino group.Diphenylphosphine sulfide (I) turned out to react with diallylamine (in the ratio 2 : 1) in benzene or dioxane at UV irradiation (200W Hg arc Lamp) or in the presence of AIBN (5 wt %, 60-65 о С) in 2-2.5 h to give diadduct II as the main product (the isolated yield 52%). For the equimolar ratio of the reagents, compound II is also the main product (Scheme 2).

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Reaction of secondary phosphine chalcogenides with diallylamine

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Organic Compounds Containing Bonds between Se or Te with P, As, Sb and Bi

Murai

2014

Patai's Chemistry of Functional Groups

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This chapter describes syntheses, structures, and reactions of the compounds with phosphorus‐selenium double bonds and with at least one carbon‐phosphorus single bond and of their heavier congeners. Among them, phosphane selenides have been the most deeply studied and used as Lewis base catalysts, metal ligands, molecular sensors, and stating materials leading to selenium‐containing nanoparticles. The coupling constants between the phosphorus and selenium atoms are informative on the basicity of the phosphanes. Phosphinoselenoic acid chlorides and secondary phosphanes are frequently used precursors to give a range of phosphinoselenoic acid derivatives, whereas selenation of dichlorophosphanes leads to phosphonoselenoic acid dichlorides, which are converted to a variety of acid derivatives. The selenation of phosphinites also gives phosphinoselenoic acid O ‐esters. Stereochemical course of the substitution reaction at P ‐chiral phosphorus center in the substitution reaction has been elucidated. Some reactions of dimers of diselenoxophosphanes such as Woollin's reagent are also shown. The chapter finally describes examples of phosphane tellurides, arsenic, antimony, and bismuth isologues of phosphane selenides, although these are fewer.

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Facile Non‐Catalyzed Synthesis of Tertiary Phosphine Sulfides by Regioselective Addition of Secondary Phosphine Sulfides to Alkenes

Малышева¹,

Гусарова²,

Artem’ev³

et al. 2014

Eur J Org Chem

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An atom‐economic green synthesis of tertiary phsophine sulfides has been developed based on catalyst‐ and solvent‐free addition of secondary phosphine sulfides to diverse terminal and internal alkenes (hept‐1‐ene, cyclohexene, styrenes, allyl alcohol, vinyl ethers, vinyl sulfides, vinyltrimethylsilane, 1‐vinylimidazoles, vinyl acetate). The reaction proceeds under mild conditions (80 °C, without solvent, 4–45 h) to afford chemo‐ and regioselectively the corresponding anti‐Markovnikov adducts in excellent to quantitative yields (50–99 %).

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One-pot synthesis of ultra-branched mixed tetradentate tripodal phosphines and phosphine chalcogenides

Cited by 12 publications

References 61 publications

Reaction of secondary phosphine chalcogenides with diallylamine

Reaction of secondary phosphine chalcogenides with diallylamine

Organic Compounds Containing Bonds between Se or Te with P, As, Sb and Bi

Facile Non‐Catalyzed Synthesis of Tertiary Phosphine Sulfides by Regioselective Addition of Secondary Phosphine Sulfides to Alkenes

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