Phosphonium Salt Ionic Liquid Research Articles

Quaternary phosphonium salt-functionalized Cr-MIL-101: A bifunctional and efficient catalyst for CO2 cycloaddition with epoxides

Integration of synergic Lewis acid sites and nucleophilic anions that can facilitate ring-opening of epoxide is a good way to develop efficient catalyst for cycloaddition of CO2 with epoxides. Herein, we prepared a novel metal-organic framework (MOF) catalyst (Cr-MIL-101-[BuPh3P]Br) through grafting quaternary phosphonium salt ionic liquid (IL) on Cr-MIL-101 by a facile post-synthetic approach. The introduction of phosphonium salt IL highly improves the catalytic activity and stability compared with the parent Cr-MIL-101-NH2. In the absence of any solvent and co-catalyst, Cr-MIL-101-[BuPh3P]Br showed excellent catalytic activity for the cycloaddition reaction under moderate reaction conditions. Under optimized conditions, the yield and TOF of propylene carbonate can be achieved 97.8% and 1086.7 h−1, respectively. This is because the synergetic interaction of dual functional sites including Cr3+ as Lewis acid sites in MOF and Br- as nucleophile in IL could promote the ring-opening of epoxide through the coordination of Cr3+ sites with O atom and the nucleophilic attack of Br- on the less sterically hindered β-carbon atom of epoxide, respectively. Comparison with other reported ILs-functionalized Cr-MIL-101 or other kinds of MOFs catalysts reveals that Cr-MIL-101-[BuPh3P]Br has superior catalytic performance and potential. Moreover, Cr-MIL-101-[BuPh3P]Br as a heterogeneous catalyst also showed good chemical stability and reusability.

Ionic Liquid Tributyl (Carboxymethyl) Phosphonium Bromide as an efficient Catalyst for the Synthesis of bis(indolyl)Methanes under Solvent-Free Conditions

A simple green synthesis of bis (indolyl)methanes involved the reaction of indole with aldehydes in the presence of a phosphonium salt ionic liquid as the catalyst. The simple experimental procedur...

ChemInform Abstract: Iron‐Catalyzed Quick Homocoupling Reaction of Aryl or Alkynyl Grignard Reagents Using a Phosphonium Ionic Liquid Solvent System.

AbstractBulky substituents decrease the yield in the presented reaction.

Iron‐catalyzed quick homocoupling reaction of aryl or alkynyl Grignard reagents using a phosphonium ionic liquid solvent system

AbstractThe iron‐catalyzed homocoupling reaction of aryl Grignard reagent was completed very quickly when the reaction was carried out in a phosphonium salt ionic liquid solvent system at 0°C for 5 min. Using a similar reaction system, the first example of the iron‐catalyzed homocoupling reaction of alkynyl Grignard reagents has also been accomplished using the ionic liquid technology. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:397–404, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20696

ChemInform Abstract: Palladium‐Catalyzed Double Carbonylation Reactions of o‐Dihaloarenes with Amines in Phosphonium Salt Ionic Liquids.

AbstractN‐Substituted phthalimides are prepared in phosphonium salt ionic liquid CYPHOSIL 102 as a solvent.

Palladium-Catalyzed Double Carbonylation Reactions of o-Dihaloarenes with Amines in Phosphonium Salt Ionic Liquids

Palladium-catalyzed double carbonylation of o-dihaloarenes with amines in phosphonium salt ionic liquids proceeds efficiently to give the corresponding N-substituted phthalimides. This process can tolerate a wide array of functional groups and affords products in excellent yields. The recyclability of the catalytic system was also investigated.

Synthesis of Chromones via Palladium-Catalyzed Ligand-Free Cyclocarbonylation of o-Iodophenols with Terminal Acetylenes in Phosphonium Salt Ionic Liquids

The highly efficient and selective palladium-catalyzed ligand-free cyclocarbonylation reaction of o-iodophenols with terminal acetylenes and CO in the phosphonium salt ionic liquid, C(14)H(29)(C(6)H(13))(3)P(+)Br(-), affords diversified chromones in good to excellent yields under atmospheric CO pressure. The ionic liquid, as the reaction medium, enhances the efficiency of the cyclocarbonylation reaction.

Syntheses of Substituted 3-Methyleneisoindolin-1-ones By a Palladium-Catalyzed Sonogashira Coupling−Carbonylation−Hydroamination Sequence in Phosphonium Salt-Based Ionic liquids

Two efficient approaches for the synthesis of isoindolin-1-one derivatives in phosphonium salt ionic liquids are described. The palladium-catalyzed carbonylation-hydroamination reaction of 1-halo-2-alkynylbenzene with amines afforded the substituted 3-methyleneisoindolin-1-ones in good yields and high selectivities in favor of the Z-isomers. The target molecules could also be synthesized by the Sonogashira coupling-carbonylation-hydroamination one-pot reaction of dihalides, alkynes, and amines. Both processes can be conducted under mild conditions and tolerate a wide array of functionalized substrates.

ChemInform Abstract: Palladium‐Catalyzed Thiocarbonylation of Iodoarenes with Thiols in Phosphonium Salt Ionic Liquids.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Palladium-Catalyzed Thiocarbonylation of Iodoarenes with Thiols in Phosphonium Salt Ionic Liquids

Trihexyl(tetradecyl)phosphonium hexafluorophosphate, a phosphonium salt ionic liquid (PSIL) is a particularly effective general reaction media for the Pd-catalyzed carbonylation reaction of iodoarenes and thiols to form thioesters. Recycling of the ionic liquid containing active Pd-catalyst was also demonstrated.

Efficient Carbonylation Reactions in Phosphonium Salt Ionic Liquids: Anionic Effects

Application of phosphonium salt ionic liquids in the carbonylation of aryl and vinyl halides is presented. Anionic effects were uncovered with the bromide ionic liquid emerging as the superior media. Acid bromide intermediates were detected in control experiments providing an extended view on the overall catalytic cycle involved. Solvent-free product isolation and recycling of the ionic liquid containing active Pd-catalyst are also demonstrated.

A Pronounced Anionic Effect in the Pd‐Catalyzed Buchwald—Hartwig Amination Reaction Revealed in Phosphonium Salt Ionic Liquids.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract, please click on HTML or PDF.

A Pronounced Anionic Effect in the Pd‐Catalyzed Buchwald–Hartwig Amination Reaction Revealed in Phosphonium Salt Ionic Liquids

AbstractThe Pd‐mediated Buchwald–Hartwig amination reaction of aryl halides in a phosphonium salt ionic liquid consisting of a trihexyl(tetradecyl)phosphonium cation with a range of anions has been investigated. A pronounced anionic effect was uncovered with the reaction proceeding readily with weakly nucleophilic diarylamines only in the presence of noncoordinating anions. A mechanism is postulated to explain these results and it involves a rate‐limiting ligand exchange step that proceeds through a dissociative pathway.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

A Mild Esterification Process in Phosphonium Salt Ionic Liquid.

For Abstract see ChemInform Abstract in Full Text.

A mild esterification process in phosphonium salt ionic liquid

A general, high yielding procedure is described for the esterification of carboxylic acids through carboxylate alkylation in phosphonium salt ionic liquid.

Heck Reactions of Aryl Halides in Phosphonium Salt Ionic Liquids: Library Screening and Applications.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Heck reactions of aryl halides in phosphonium salt ionic liquids: library screening and applications

The Heck cross-coupling of aryl iodides and bromides with olefins proceeds in the phosphonium salt ionic liquid trihexyl(tetradecyl)phosphonium chloride (THP-Cl) in excellent yields. Furthermore, it is shown that the counter anion matched to the phosphonium cation exerts a measurable effect on the overall yield.

Suzuki Cross‐Coupling Reactions of Aryl Halides in Phosphonium Salt Ionic Liquid under Mild Conditions.

The Suzuki cross-coupling of aryl boronic acids with aryl halides, including aryl chlorides, proceeds in the phosphonium salt ionic liquid tetradecyltrihexylphosphonium chloride under mild conditions.

Suzuki cross-coupling reactions of aryl halides in phosphonium salt ionic liquid under mild conditions.

The Suzuki cross-coupling of aryl boronic acids with aryl halides, including aryl chlorides, proceeds in the phosphonium salt ionic liquid tetradecyltrihexylphosphonium chloride under mild conditions.