Preparation and Reactivity of Chalcogenyl Phosphonates and Phosphane Oxides

Silveira, Cláudio C.; Rinaldi, Francieli; Guadagnin, Rafael C.

doi:10.1002/ejoc.200700388

Cited by 28 publications

(15 citation statements)

References 66 publications

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“…The crude product was recrystallized (CH 2 Cl 2 /Et 2 O, 1:9) to give pure diphenyl{[(p-tolylsulfonyl)oxy]methyl}phosphane oxide as a white solid (3.93 g, 71 %). [36] The analytical data for this compound match that previously reported. [36] To a solution of the diphenyl{[(p-tolylsulfonyl)oxy]methyl}phosphane oxide (3.86 g, 10.0 mmol) in acetone (200 mL) was added sodium iodide (5.99 g, 40.0 mmol).…”

Section: Preparation Of Diethyl (1-iodopent-4-enyl)phosphonate (2d)supporting

confidence: 70%

“…[36] The analytical data for this compound match that previously reported. [36] To a solution of the diphenyl{[(p-tolylsulfonyl)oxy]methyl}phosphane oxide (3.86 g, 10.0 mmol) in acetone (200 mL) was added sodium iodide (5.99 g, 40.0 mmol). The mixture was heated to 75°C for 24 h, quenched with sodium thiosulfate (saturated aqueous, 100 mL), and extracted with ethyl acetate (3 ϫ 100 mL).…”

Section: Preparation Of Diethyl (1-iodopent-4-enyl)phosphonate (2d)supporting

confidence: 70%

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Synthesis of Cyclopropane‐Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds

et al. 2011

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The radical coupling of α-or β-iodo phosphorus compounds such as iodo phosphonate, iodo phosphane oxide, and iodo phosphonothioate with butenylindium species, prepared by transmetalation between a (cyclopropylmethyl)stannane and InBr 3 , afforded the corresponding cyclopropylmethylated products. The radical reaction was initiated by the radical species generated from butenylindium assisted by a small amount of oxygen. Butenylindium works not only as a cyclopropylmethylating reagent, but also as a radical initiator. For

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Section: Preparation Of Diethyl (1-iodopent-4-enyl)phosphonate (2d)supporting

confidence: 70%

Section: Preparation Of Diethyl (1-iodopent-4-enyl)phosphonate (2d)supporting

confidence: 70%

Synthesis of Cyclopropane‐Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds

et al. 2011

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“…[31][32][33][34][35][36][37][38] In this regard, our continuous interests in the synthesis of organochalcogen compounds prompted us to access symmetrical and unsymmetrical vinyl suldes by a straightforward approach, using a Wittig-Horner reaction, as precursors of products carrying a higher oxidation state on sulfur. 39,40 In this sense, photoactive divinyl suldes and sulfones have been obtained. 31,41 However, there is a lack of information on the rationalization of comparative electronic effects exerted by organosuldes, sulfoxides and sulfones on excited and ground states of pushpull p-conjugated structures.…”

Section: Introductionmentioning

confidence: 99%

Dipolar vinyl sulfur fluorescent dyes. Synthesis and photophysics of sulfide, sulfoxide and sulfone based D–π–A compounds

et al. 2017

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“…38,[61][62][63][64] Analysis of the 1 H NMR and 13 C NMR spectra showed that all alkene compounds presented data in full agreement with their assigned structures. The stereochemistry of the obtained alkenes was easily established.…”

Section: Resultsmentioning

confidence: 97%

Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

Silveira¹,

Mendes²,

Wolf³

2010

J. Braz. Chem. Soc.

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Este trabalho descreve um novo método para a reação de acoplamento entre selenetos e teluretos vinílicos e reagentes de Grignard, catalisada por Fe(acac) 3 e à temperatura ambiente. A reação ocorre com retenção da configuração, fornecendo os respectivos alquenos em bons a excelentes rendimentos. Este método também é eficiente para a reação de acoplamento de calcogenetos bisvinílicos com reagentes de Grignard.A general new method for the cross-coupling reaction between vinylic selenides and tellurides and Grignard reagents catalyzed by Fe(acac) 3 at room temperature is described. This reaction proceeded with retention of configuration, providing the respective alkenes in good to excellent yields. This method is also efficient for the coupling reaction of divinyl chalcogenides with Grignard reagents. Keywords: iron-catalyzed, vinylic chalcogenides, cross-coupling, Grignard reagents IntroductionOrganochalcogenium compounds became the key component of a variety of versatile and useful reagents for organic synthesis. The multiple applications of organochalcogenium chemistry have been well described in a number of review articles 1-6 and books. 7-11 Functionalized alkynyl 12-18 and alkenyl [19][20][21][22][23] chalcogenides have a great potential in organic synthesis, since they are valuable intermediates for the selective preparation of several organic compounds.Among the many applications of vinylic selenides, divinylic selenides and vinylic sulfides, the cross-coupling reaction with Grignard reagents catalyzed by Ni 18,24-27 and Pd 28,29 to give the corresponding cross-coupled products, has been described. On the other hand, Pd 19,30 and Ni 24,[31][32][33] catalyzed cross coupling reactions and tellurium/metal exchange reactions [34][35][36][37][38][39][40][41][42] are demonstrative of the usefulness of vinylic tellurides.Transition-metal-catalyzed C-C bond coupling reactions are very important in many areas of science. 43,44 Most current methods require expensive transitionmetal catalysts and ligands. However, in the last years Fe-catalyzed C-C bond cross coupling reactions of vinylic substrates and Grignard reagents became a subject of intense interest. [45][46][47][48][49][50][51] The vinylic counterpart is quite broad in scope, since vinylic halides, triflates, sulfonates, tosylates and enol phosphates can be used. [45][46][47][48][49][50][51] In continuation to our interest on the synthesis and synthetic applications of vinylic chalcogenides 52-58 we decided to study the feasibility of their use in cross coupling reaction with Grignard species catalyzed by iron. To the best of our knowledge, iron catalysts have never been used for the coupling of vinylic selenides and tellurides as electrophiles. The possible use of iron catalysts would represent a great improvement over the high cost of palladium precursors and from the concerns about the toxicity of nickel salts. In light of the above comments it is of interest to design a simple, efficient, and versatile method for the stereoselective coupling of vinylic se...

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Preparation and Reactivity of Chalcogenyl Phosphonates and Phosphane Oxides

Cited by 28 publications

References 66 publications

Synthesis of Cyclopropane‐Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds

Synthesis of Cyclopropane‐Containing Phosphorus Compounds by Radical Coupling of Butenylindium with Iodo Phosphorus Compounds

Dipolar vinyl sulfur fluorescent dyes. Synthesis and photophysics of sulfide, sulfoxide and sulfone based D–π–A compounds

Iron-catalyzed coupling reactions of vinylic chalcogenides with Grignard reagents

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