Hydroxyferrocene as a prochiral analog of phenols: cyclopalladation of a mixed phosphite ester of hydroxyferrocene

Troitskaya, L. L.; Ovseenko, S. T.; Slovokhotov, Yurii L.; Neretin, Ivan S.; Sokolov, V. I.

doi:10.1016/s0022-328x(01)01228-1

Cited by 11 publications

(4 citation statements)

References 13 publications

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“…93 Not all attempts at asymmetric induction during the synthesis of planar chiral palladacycles have met with success. The C-H activation of a prochiral ferrocenylamine with a chiral sulfoxide palladium-containing complex led to racemic palladacycle 79, 94 and the use of a chiral yet racemic phosphite as directing group afforded the metallacycle 80 95 with a de ) 0% (Scheme 25). tiopure amines (formed by either asymmetric synthesis or resolution).…”

Section: Planar Chiral Palladacyclesmentioning

confidence: 99%

The Potential of Palladacycles: More Than Just Precatalysts

2005

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Section: Planar Chiral Palladacyclesmentioning

confidence: 99%

The Potential of Palladacycles: More Than Just Precatalysts

2005

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“…Исходный 2-хлор-4,5-диметил-1,3,2-диоксафосфолан получен на основе реакции 2,3-бутандиола с трихлоридом фосфора в присутствии N,N-диметил-анилина [20]; исходный 2,2,3,3,4,4, Тестирование экстракционных свойств 4,5-диметил-2-(2,2,2-трифторэтокси)-1,3,2диоксафосфолана (3). При смешивании фосфолана (3) и азотнокислого раствора урансодержащего товарного десорбата образовалось две фазы: органическая и водная.…”

Section: экспериментальная частьunclassified

Synthesis and study of the extraction properties ofnew phosphorus-containing extractants of heavy metals

Bishimbaeva

Nalibaeva²,

Сайдуллаева

et al. 2021

Izvestiâ vuzov. Prikladnaâ himiâ i biotehnologiâ

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The metallurgical industry is one of the cornerstones of contemporary chemical science and industry and it is developing rapidly in many countries. The widespread introduction of metal extraction, concentration and separation as the most productive methods entails the need to search for and create new effective metal extractants. Among the compounds, suitable for use as extractants, the most widespread are organic phosphites and phosphates, which allow performing extraction processes with good selectivity and efficiency. The purposes of this article include finalizing the optimal synthesis conditions and developing larger batches of 4,5-dimethyl-2-(2,2,2-trifluoroethoxy)-1,3,2-dioxaphospholane and 5,5-dimethyl-2-(2,2,3,3,4,4,5,5- octafluoropentoxy)-1,3,2-dioxaphosphorinane, and study of the extraction properties of the obtained phosphorus- containing heterocyclic compounds in the separation of uranium from the commercial desorbate. The synthesis of new representatives of the indicated polyfluoroalkylated five- and six-membered heterocyclic phosphorus compounds was conducted using the interaction of 2-chloro-1,3,2-dioxaphospholane with trifluoroethanol and the substitution–cyclization reaction of polyfluoroalkylated dichlorophosphite with 2,2-dimethyl- 1,3-propanediol. Reactions easily proceed in triethylamine–hexane or pyridine–diethyl ether systems at temperatures ranging between minus ten to room temperature, with the output of target heterocycles of 53–57%. The studies of extraction properties of synthesized poly-fluorinealkylated dioxaphospholane and dioxaphosphorinane show that the use of these phosphorus-containing heterocyclic compounds as extractants allows extracting a technically valuable metal up to 12.4 and 15.2%, respectively. Nitric and sulfuric acid solutions of commercial desorbate of hydrometallurgical production in Kazakhstan were used as feedstock in the extraction process.

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“…However, in the cyclopalladation of the diphosphine HL 27 with the more rigid dibenzyl skeleton by treatment with the same reagent, a high yield of the PCP-complex 27a (75%) is attained under milder conditions. 60,61 Nitrile palladating agents are used somewhat more rarely to prepare monocyclic PC-complexes, although they are rather effective (with rare exceptions 140 ) towards the activation of the C(sp 2 )7H and C(sp 3 )7H bonds (see Table 1). To attain high yields in the ortho-palladation of monodentate benzylphosphines (83% ± 85%) 113 and phosphites (70% ± 90%), 56,138,141,142 heating is usually required; however, cyclopalladation of the phosphaalkene HL 40 with the supermesityl substituent proceeds even at 20 8C (the yield of 40 is 97%).…”

Section: A Standard Routes and Classical Reagentsmentioning

confidence: 99%

“…This function can be performed by phosphine ligands themselves; thus the isolation of the corresponding phosphonium salts as the chloride, [HPBu The necessity of adding a base arises in the case of lowreactivity ligands. Usually, sodium acetate is used as the base; triethylamine 82 or potassium carbonate 140 are less effective and are used less often. Examples of substantial acceleration of the process following the introduction of a proton acceptor are few and mainly refer to reactions of benzylphosphines.…”

Section: A Standard Routes and Classical Reagentsmentioning

confidence: 99%

Phosphapalladacycles: preparation routes

Dunina¹,

Gorunova²

2004

Russ. Chem. Rev.

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The review considers methods of synthesis of cyclo-The review considers methods of synthesis of cyclopalladated compounds of the PC-and PCP-type including intra-palladated compounds of the PC-and PCP-type including intramolecular activation of the C molecular activation of the C7 7H bonds in the P-donor ligands, H bonds in the P-donor ligands, oxidative addition of preliminarily functionalised substrates to oxidative addition of preliminarily functionalised substrates to palladium( palladium(0 0), transmetallation of lithiated compounds, chelation), transmetallation of lithiated compounds, chelation of phosphine-substituted phosphorus ylides, and some non-stand-of phosphine-substituted phosphorus ylides, and some non-standard processes resulting in a new ligand formation on a metal ard processes resulting in a new ligand formation on a metal template. Particular attention has been given to the structural template. Particular attention has been given to the structural factors and experimental conditions that determine the feasibility factors and experimental conditions that determine the feasibility of direct cyclopalladation of mono-and bidentate phosphines, of direct cyclopalladation of mono-and bidentate phosphines, phosphites and phosphinites. The bibliography includes 384 phosphites and phosphinites. The bibliography includes 384 references. references.

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Hydroxyferrocene as a prochiral analog of phenols: cyclopalladation of a mixed phosphite ester of hydroxyferrocene

Cited by 11 publications

References 13 publications

The Potential of Palladacycles: More Than Just Precatalysts

The Potential of Palladacycles: More Than Just Precatalysts

Synthesis and study of the extraction properties ofnew phosphorus-containing extractants of heavy metals

Phosphapalladacycles: preparation routes

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