ChemInform Abstract: Pseudo Five‐Component Synthesis of 3‐(Hetero)arylmethyl‐2,5‐di(hetero)‐aryl‐Substituted Thiophenes via Sonogashira—Glaser Cyclization Sequence.

Klukas, Fabian; Perkampus, J; Urselmann, Dominik; Mueller, Thomas

doi:10.1002/chin.201520119

Cited by 2 publications

(2 citation statements)

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“…Likewise, the Müller group disclosed a rapid access to intensively blue luminescent 2,5-di(hetero)arylfurans when potassium hydroxide was used as the bifunctional nucleophile [86]. The same concept was applied to the synthesis of 3-(hetero)arylmethyl-2,5-di(hetero)aryl-substituted thiophenes in the sense of a pseudo five-component process by employing (hetero)aryl methylthiols as masked dinucleophilic substrates [87]. Table 5) [88].…”

Section: Methodsmentioning

confidence: 99%

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Lessing

Müller

2015

Applied Sciences

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Sequentially Pd-catalyzed processes are excellent entries to heterocycle synthesis. The broad mechanistic variety combined with often very mild reaction conditions allow the concatenation of elementary organic and organometallic steps to novel sequences in the sense of one-pot domino and multicomponent reactions. Given the numerous opportunities of alkyne coordination and their Pd-mediated transformations, alkynylation and carbometallation play a key role, both for purely organometallic sequences as well as in those processes that are intercepted by cyclocondensation. Pd-catalyzed aminations also find more and more entry into novel heterocycle syntheses based upon this theme.

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Section: Methodsmentioning

confidence: 99%

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Lessing

Müller

2015

Applied Sciences

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“…Whereas a large number of star-shaped [10,11] and discotic [12,13] π-conjugated systems have been investigated, compounds with a thiophene based core appear only scarcely [13,14]. 1,3,5-Tris-(2-thienyl)benzene has been prepared via cyclocondensation of 2-acetylthiophenes [15], a recent approach is based on the addition of benzenetri(methylthiol) to diynes [16]. Extension of the conjugated system is possible via pd-catalyzed coupling reactions [17].…”

Section: Introductionmentioning

confidence: 99%

2-{3,5-Bis-[5-(3,4-didodecyloxyphenyl)thien-2-yl]phenyl}-5-(3,4-didodecyloxyphenyl)thiophene

Jochem

Detert

2021

Molbank

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Star-shaped compounds are widely recognized as emerging materials for optical and electrical applications and as scaffolds of discotic liquid crystal. While the C3-symmetrical tri(phenylthienyl)benzene is the core for several electroopotical materials, no liquid crystal with this scaffold has yet been reported. Acid-catalyzed cyclocondensation of bromoacetylthiophene gives a C3-symmetrical star, threefold Suzuki coupling results in extension of the conjugated system. With 3,4-didodecylocyphenyl boronic acid, a star with a large rigid conjugated system and flexible aliphatic periphery is obtained. Differentials scanning calorimetry and polarized optical microscopy reveal an enantiotropic mesophase from 66 °C to 106 °C.

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ChemInform Abstract: Pseudo Five‐Component Synthesis of 3‐(Hetero)arylmethyl‐2,5‐di(hetero)‐aryl‐Substituted Thiophenes via Sonogashira—Glaser Cyclization Sequence.

Abstract: Pseudo Five-Component Synthesis of 3-(Hetero)arylmethyl-2,5-di(hetero)-aryl--Substituted Thiophenes via Sonogashira-Glaser Cyclization Sequence. -(KLUKAS, F.; PERKAMPUS, J.; URSELMANN, D.; MUELLER*, T. J. J.; Synthesis 46 (2014) 24, 3415-3422, http://dx.

Cited by 2 publications

References 1 publication

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

Sequentially Palladium-Catalyzed Processes in One-Pot Syntheses of Heterocycles

2-{3,5-Bis-[5-(3,4-didodecyloxyphenyl)thien-2-yl]phenyl}-5-(3,4-didodecyloxyphenyl)thiophene

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