Phosphonium Salts and P-Ylides

Odinets, Irina L.

doi:10.1039/9781849730839-00094

Cited by 5 publications

(4 citation statements)

References 192 publications

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“…These pathways have been documented well by Yavari and Ramazani, using DMAD and triphenylphosphine in the presence of pronucleophiles. Ramazani and Odinets have written thorough Reviews providing further details. , …”

Section: Ylides Formed Through Nucleophilic Addition Of Phosphinementioning

confidence: 99%

“…Ramazani and Odinets have written thorough Reviews providing further details. 759,799 A general reaction mechanism can be depicted with initial nucleophilic addition of the tertiary phosphine into DMAD, facilitating the generation of a zwitterion (Scheme 712). Subsequent activation of the pronucleophile through deprotonation triggers nucleophilic addition into the resulting vinyl phosphonium species 452, affording the phosphorus ylide 453.…”

Section: Ylides From Graminementioning

confidence: 99%

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Phosphine Organocatalysis

et al. 2018

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The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

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Section: Ylides Formed Through Nucleophilic Addition Of Phosphinementioning

confidence: 99%

Section: Ylides From Graminementioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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“…However, recently they have attracted much more attention as exciting catalyst precursors for different types of cross coupling reactions [1][2][3]. Phosphonium salts have a range of advantages, including the existence of a wide variety of organic derivatives, functionalized types of branches and their use as catalysts in several organic reactions, including oxidation.…”

Section: Introductionmentioning

confidence: 99%

From phosphonium salts to binuclear ortho-palladated phosphorus ylides

2015

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“…The success of using phosphorus-containing cations as OSDA for zeolite crystallization has moved us to look for different alternatives of organophosphorous cations that are easy and safe to prepare. Then, we found in literature that Wittig-like cations can be quantitatively prepared from the commercially available aminophosphines resulting in phosphorus-containing cations. − These new organocations are related to phosphazenes and tetraalkylphosphonium, since they contain P–N and P–C bonds (see Figure S1). On those bases, we have developed a new family of amino-phosphonium cations that introduce interesting features from the point of view of OSDAs for zeolite synthesis.…”

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A New Microporous Zeolitic Silicoborate (ITQ-52) with Interconnected Small and Medium Pores

et al. 2014

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ABSTRACT:A new zeolite (named as ITQ-52) having large cavities and small and medium channels has been synthesized. This was achieved by using a new family of aminophosphonium cations as organic structure directing agent (OSDA). These cations contain P-C and P-N bonds, and therefore they lie between previously reported P-containing OSDA, such as tetraalkylphosphonium and phosphazenes. In this study, it has been found that 1,4-butane-diylbis[tris(dimethylamino)]phosphonium dication is a very efficient OSDA for crystallization of several zeolites, and in some particular conditions, the new zeolite ITQ-52 was synthesized as a pure phase. The structure of ITQ-52 has been solved using high resolution synchrotron X-Ray powder diffraction data of the calcined solid. This new zeolite crystallizes in the space group I2/m, with cell parameters a = 17.511 Å, b = 17.907 Å, c = 12.367 Å and β = 90.22 º. The topology of ITQ-52 can be described as a replication of a Composite Building Unit with ring notation [4 3 5 4 6 1 ] that gives rise to the formation of an interconnected 8R and 10R-channel system. Typically, zeolites can be described as crystalline silicabased microporous solids that can carry out a myriad of different processes when doped with the appropriated active sites, such as Al, B, Ga, Ge, Ti, Sn, etc. The catalytic performance of the final porous solids depends mainly on the nature of the heteroatom as well as on their structural pore topologies. Zeolites have been applied for gas adsorption, separation, catalysis, encapsulation or controlled release of molecules, among others, some of them are of industrial application. [1][2][3][4][5][6][7][8][9] There is no doubt that this is the driving force for synthesizing new zeolite structures.Most of the zeolites described in the literature have been obtained by employing tetraalkylammonium cations as organic structure directing agents (OSDAs). 10-13 Recently, we have reported a number of new zeolites synthesized by using tetraalkylphosphonium cations 14 15 and ITQ-49 17 ) or phosphazenes (ITQ-47 18 ) as OSDAs. The success of using phosphorous-containing cations as OSDA for zeolite crystallization has moved us to look for different alternatives of organophosphorous cations that are easy and safe to prepare. Then, we found in literature that Wittig-like cations can be quantitatively prepared from the commercially available aminophosphines resulting in phosphorous containing cations. [19][20][21][22] These new organocations are related to phosphazenes and tetraalkylphosphonium, since they contain P-N and P-C bonds (see fig. S1 in Supporting Information). On those bases, we have developed a new family of amino-phosphonium cations that introduce interesting features from the point of view of OSDAs for zeolite synthesis. Then, the amino-phosphonium cationic compounds have been used for zeolite synthesis, and here we describe the synthesis and crystal structure of a new zeolite, named as ITQ-52, that was obtained by using 1,4-butane-diylbis[tris(dimethylamino)]phosphonium di...

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Phosphonium Salts and P-Ylides

Cited by 5 publications

References 192 publications

Phosphine Organocatalysis

Phosphine Organocatalysis

From phosphonium salts to binuclear ortho-palladated phosphorus ylides

A New Microporous Zeolitic Silicoborate (ITQ-52) with Interconnected Small and Medium Pores

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