Three-Component Reaction between Vinyl Ethers, Secondary Phosphines, and Elemental Selenium: One-Pot Synthesis of 1-(Alkoxy)ethyl and 1-(Aryloxy)ethyl Phosphinodiselenoates

Гусарова, Н. К.; Artem’ev, Alexander V.; Опарина, Л. А.; Kolyvanov, Nikita A.; Малышева, С. Ф.; Vysotskaya, O. V.; Трофимов, Б. А.

doi:10.1055/s-0031-1289655

Cited by 6 publications

References 5 publications

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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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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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Reaction of Vinyl Selenides with Secondary Phosphines and Elemental Selenium: One‐Pot Selective Synthesis of a New Family of Diselenophosphinic Se‐Esters

Artem’ev

Чернышeва

Гусарова

et al. 2014

Heteroatom Chemistry

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Alkyl vinyl selenides react with diverse secondary phosphines and elemental selenium in a 1.1:1:2 molar ratio (120–124°C, 20–40 min, 1,4‐dioxane) to afford selectively earlier unknown diselenophosphinic Se‐esters, R2P(Se)SeCH(Me)SeR´, in 82–99% yield. This three‐component atom‐economic reaction proceeds via intermediate formation of diselenophosphinic acid R2P(Se)SeH (generated from secondary phosphine and selenium), which adds to the double bond of vinyl selenide in a Markovnikov manner to give the target products.

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Expedient Route to Chalcogenophosphinates with Glucose Moieties via Todd–Atherton‐Like Coupling between Secondary Phosphine Chalcogenides and Diacetone‐d‐Glucose in the CCl₄/Et₃N System

Volkov

Иванова

Гусарова

et al. 2015

Heteroatom Chemistry

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Secondary phosphine chalcogenides react with diacetone‐d‐glucose (DAG) in the system CCl4/Et3N (70°C, 4–24 h) to afford DAG chalcogenophosphinates in up to 79% yield, thus paving a short way to optically active chalcogenophosphinates with glucose moieties. As an example, a mild regioselective hydrolysis (70°C, aqueous MeCOOH) of DAG bis(2‐phenylethyl)selenophosphinate) obtained leads to monoacetone‐d‐glucose bis(2‐phenylethyl)selenophosphinate.

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Three-Component Reaction between Vinyl Ethers, Secondary Phosphines, and Elemental Selenium: One-Pot Synthesis of 1-(Alkoxy)ethyl and 1-(Aryloxy)ethyl Phosphinodiselenoates

Cited by 6 publications

References 5 publications

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

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

Reaction of Vinyl Selenides with Secondary Phosphines and Elemental Selenium: One‐Pot Selective Synthesis of a New Family of Diselenophosphinic Se‐Esters

Expedient Route to Chalcogenophosphinates with Glucose Moieties via Todd–Atherton‐Like Coupling between Secondary Phosphine Chalcogenides and Diacetone‐d‐Glucose in the CCl₄/Et₃N System

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Three-Component Reaction between Vinyl Ethers, Secondary Phosphines, and Elemental Selenium: One-Pot Synthesis of 1-(Alkoxy)ethyl and 1-(Aryloxy)ethyl Phosphinodiselenoates

Cited by 6 publications

References 5 publications

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

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

Reaction of Vinyl Selenides with Secondary Phosphines and Elemental Selenium: One‐Pot Selective Synthesis of a New Family of Diselenophosphinic Se‐Esters

Expedient Route to Chalcogenophosphinates with Glucose Moieties via Todd–Atherton‐Like Coupling between Secondary Phosphine Chalcogenides and Diacetone‐d‐Glucose in the CCl4/Et3N System

Contact Info

Product

Resources

About

Expedient Route to Chalcogenophosphinates with Glucose Moieties via Todd–Atherton‐Like Coupling between Secondary Phosphine Chalcogenides and Diacetone‐d‐Glucose in the CCl₄/Et₃N System