Palladium(II)‐ und Platin(IV)‐Komplexe von 1.2‐Bis‐phenyläthinyl‐benzol

Müller, Eugen; Munk, Kurt; Ziemek, Peter; Sauerbier, Michael

doi:10.1002/jlac.19687130105

Cited by 24 publications

(4 citation statements)

References 2 publications

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“…The resulting vinyl cation intermediates could then open up a new field of chemistry as their generation does not require the presence of at least one terminal alkyne in the diyne system as in dual gold catalysis . Earlier efforts by Müller and co‐workers, with these substrates using stoichiometric amounts of PdCl 2 , PtCl 2 , PtCl 4 , AuCl 3 , AuCl, or Na[AuCl 4 ] all showed low selectivity (even worse, for gold “catalysts”, a yield of only 1 % was achieved, which corresponds to 0.02 turnovers, that is, a 50‐fold excess of gold with regard to the product formed); the authors proposed a radical mechanism and thus subsequently also investigated photochemical conversions without metal catalyst, which delivered a different product in 3 % yield . In 1991, Blum and Vollhardt succeeded in improving Müller's conditions, achieving a yield of 80 % under quite forcing conditions (120 °C) in a biphasic water/dichloromethane mixture with a phase‐transfer catalyst and H 2 [PdCl 4 ] (5 mol %) after 16 h; again, no mechanistic insight was obtained .…”

Section: Methodsmentioning

confidence: 99%

On the Gold‐Catalyzed Generation of Vinyl Cations from 1,5‐Diynes

et al. 2017

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Conjugated 1,5-diynes bearing two aromatic units at the alkyne termini were converted in the presence of a gold catalyst. Under mild conditions, aryl-substituted dibenzopentalenes were generated. Calculations predict that aurated vinyl cations are key intermediates of the reaction. A bidirectional approach provided selective access to the angular annulated product in high yield, which was explained by calculations.

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Section: Methodsmentioning

confidence: 99%

On the Gold‐Catalyzed Generation of Vinyl Cations from 1,5‐Diynes

et al. 2017

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“…17 1,2-Dibromobenzene (1.21 mL, 10 mmol) was coupled to phenylacetylene (3.29 mL, 30 mmol) as described above using copper(I) iodide (0.23 g, 1.2 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.42 g, 0.6 mmol), benzene (5 mL), and triethylamine (8.5 mL, 60 mmol) in a screw cap tube that was then sealed with a Teflon screw cap. The reaction mixture was stirred at 60°C for 1 day.…”

Section: General Procedures For the Coupling Of A Terminal Alkyne Withmentioning

confidence: 97%

Synthesis and Testing of Nonhalogenated Alkyne-Containing Flame-Retarding Polymer Additives

Morgan

Tour

1998

Macromolecules

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In this paper, the synthesis and thermal properties of several alkyne-containing materials are discussed. The materials were synthesized using palladium/copper-or palladium/zinc-mediated crosscoupling reactions between multibrominated aromatics and phenylacetylene. Therefore, in one step, commercially available brominated flame retardants can be converted into nonhalogenated high-char materials using transition metal catalysis. The materials synthesized included polymers, oligomers, carbonates, and diphenyl ethers. The thermal properties of the synthesized materials were studied using differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA). In general, the DSC and TGA data showed that the synthesized materials were all high-char-yielding materials. Further, DSC data showed that the materials which had o-dialkyne substitutions (enediyne systems) generally cross-linked at lower temperatures than materials that had m-dialkynes. However, TGA showed that the materials with ortho substitutions, especially those with multiple ortho substitutions, generally had higher char yields than those with meta substitutions. The materials were blended into polycarbonate and tested for ignition resistance using the UL-94 flame test. Alkyne-containing oligomer 9, used in conjunction with 0.5 wt % of a bromide-containing flame retardant, provided flame retardancy in polycarbonate according to the UL-94 test. This indicates that alkyne-containing materials, acting as condensed phase flame retardants, can substantially lower the amount of halogen content needed for flame retardancy in polycarbonate.

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“…The known platinum-mediated reactions needed between 50 and 100 mol % of platinum “catalyst”, but only 1% yield of the dibenzopentalene was obtained; this corresponds to 0.02 turnovers of the catalytic cycle. Furthermore, several other “side products” in fact were the major products. − Also, the B(C 6 F 5 ) 3 -catalyzed reaction needs to be conducted in the glovebox, and this superstrong Lewis acid catalyst has a very limited functional group tolerance. The product had to be separated from undesired side products .…”

Section: Extended Anellated Aromatic Systemsmentioning

confidence: 99%

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

et al. 2020

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Often stoichiometric amounts of gold find use in materials science; occasionally gold is even used as a support. This review discusses the contributions of gold catalysis, both homogeneous and heterogeneous, to the field of materials science. One topic is the synthesis of polymers, including nanowires and polyesters, the postcyclization of polymers, polymerization by cyclopropanation, and gold-catalyzed radical polymerization reactions. Other topics are dyes, phosphonium salts, and a wide range of extended conjugated π-systems, the latter ranging from acenes, pentalene derivatives, and different heterocyclic π-systems to fascinating applications in the synthesis of helical anellated aromatic molecules. The existing contributions clearly demonstrate the potential of gold catalysis for significant future impulses for the field of materials science.

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Palladium(II)‐ und Platin(IV)‐Komplexe von 1.2‐Bis‐phenyläthinyl‐benzol

Cited by 24 publications

References 2 publications

On the Gold‐Catalyzed Generation of Vinyl Cations from 1,5‐Diynes

On the Gold‐Catalyzed Generation of Vinyl Cations from 1,5‐Diynes

Synthesis and Testing of Nonhalogenated Alkyne-Containing Flame-Retarding Polymer Additives

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

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