Synthesis of symmetrical terphenyl derivatives by PdCl<sub>2</sub>-catalyzed Suzuki–Miyaura reaction of dibromobenzene using 3-(diphenylphosphino)propanoic acid as a ligand

Gu, Ning; Liu, Yashuai; Liu, Ping; Ma, Xinbin; Liu, Yan

doi:10.1080/00397911.2015.1126606

Cited by 7 publications

(2 citation statements)

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“…Several symmetrical and unsymmetrical substituted p-terphenyls were synthesized by palladium-catalyzed Suzuki-Miyaura coupling using arylboronic acids and aryl halides. [27][28][29][30][31] Furthermore, the water-soluble 2 N 2 O-salen was used as an efficient ligand to construct pterphenyl scaffolds via Pd-catalyzed Suzuki-Miyaura coupling of dibromobenzene with different aryl boronic acids. [32] In 2013, Wang and others developed the synthesis of p-terphenyls by Pd-catalyzed Stille cross-coupling of boron and tin-cored substrates with aryl bromide followed by Pd-catalyzed Suzuki-Miyaura cross-coupling of earlier coupling product with aryl bromide.…”

Section: Introductionmentioning

confidence: 99%

“…In literature, a number of classical and non‐classical approaches are available for the construction of p ‐terphenyls and most of them are associated with transition metal‐catalyzed cross‐coupling reactions. Several symmetrical and unsymmetrical substituted p ‐terphenyls were synthesized by palladium‐catalyzed Suzuki‐Miyaura coupling using arylboronic acids and aryl halides . Furthermore, the water‐soluble 2 N 2 O‐salen was used as an efficient ligand to construct p ‐terphenyl scaffolds via Pd‐catalyzed Suzuki‐Miyaura coupling of dibromobenzene with different aryl boronic acids .…”

Section: Introductionmentioning

confidence: 99%

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Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Chandrasekar

Singh

2020

ChemistrySelect

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A metal-free approach for the synthesis of p-terphenyls 7 a-i and cyclic p-terphenyls 9 ad and 11 ad is described via carbanion induced ring transformation reaction of 6-biphenyl-2H-pyran-2-ones 5 with malononitrile 6, cyclohexanone 8 and 1,4-cyclohexanedione monoethylene ketal 10 respectively. Additionally, the base-mediated ring transformation reactions were working smoothly under mild reaction conditions and ring transformation products 7, 9 and 11 were isolated in good to excellent yields. The synthetic approach provides the flexibility of introducing of both electron-withdrawing and-donating functionalities in p-terphenyl architecture. Moreover, the photo physical properties of compounds 7, 9 and 11 were analyzed using UV-visible and Fluorescence Spectroscopy. p-Terphenyls 7 c showed cyan fluorescence in chloroform (λ max (em): 508 nm) and acetonitrile (λ max (em): 420 nm) while cyclic p-terphenyl 9 a showed blue fluorescence in chloroform and 1,4-dioxane (λ max (em): 470 nm). Similarly, compound 11 a showed blue fluorescence in chloroform (λ max (em): 468 nm) and 1,4-dioxane (λ max (em): 473 nm). Additionally, the thermal stability of synthesized cyclic p-terphenyls 11 a, 11 c and 11 d were also studied using TG and DTA techniques.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Chandrasekar

Singh

2020

ChemistrySelect

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ChemInform Abstract: Synthesis of Symmetrical Terphenyl Derivatives by PdCl₂‐Catalyzed Suzuki—Miyaura Reaction of Dibromobenzene Using 3‐(Diphenylphosphino)propanoic Acid as a Ligand.

Liu

et al. 2016

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Ring Closing Metathesis Approach for the Synthesis of o‐Terphenyl Derivatives

Karmakar

Mandal

2019

Eur J Org Chem

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A linear synthesis of o‐terphenyl derivatives has been delineated using ring closing metathesis (RCM) as the key step. In this approach, benzil derivatives upon allyl Grignard addition provides diphenyl‐1,2‐diallyl dihydroxy derivatives which undergo ring closing metathesis to afford tetrahydro terphenyl derivatives. Aromatization‐driven dehydration then leads to a diverse set of electron rich and electron deficient o‐terphenyls. Furthermore, oxidative coupling of electron rich o‐terphenyls provides the corresponding triphenylene derivatives.

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Synthesis of symmetrical terphenyl derivatives by PdCl₂-catalyzed Suzuki–Miyaura reaction of dibromobenzene using 3-(diphenylphosphino)propanoic acid as a ligand

Cited by 7 publications

References 34 publications

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

ChemInform Abstract: Synthesis of Symmetrical Terphenyl Derivatives by PdCl₂‐Catalyzed Suzuki—Miyaura Reaction of Dibromobenzene Using 3‐(Diphenylphosphino)propanoic Acid as a Ligand.

Ring Closing Metathesis Approach for the Synthesis of o‐Terphenyl Derivatives

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Synthesis of symmetrical terphenyl derivatives by PdCl2-catalyzed Suzuki–Miyaura reaction of dibromobenzene using 3-(diphenylphosphino)propanoic acid as a ligand

Cited by 7 publications

References 34 publications

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

Metal‐Free Synthesis of Thermally Stable Fluorescent p‐Terphenyls by Ring Transformation of 2H‐Pyran‐2‐ones

ChemInform Abstract: Synthesis of Symmetrical Terphenyl Derivatives by PdCl2‐Catalyzed Suzuki—Miyaura Reaction of Dibromobenzene Using 3‐(Diphenylphosphino)propanoic Acid as a Ligand.

Ring Closing Metathesis Approach for the Synthesis of o‐Terphenyl Derivatives

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Synthesis of symmetrical terphenyl derivatives by PdCl₂-catalyzed Suzuki–Miyaura reaction of dibromobenzene using 3-(diphenylphosphino)propanoic acid as a ligand

ChemInform Abstract: Synthesis of Symmetrical Terphenyl Derivatives by PdCl₂‐Catalyzed Suzuki—Miyaura Reaction of Dibromobenzene Using 3‐(Diphenylphosphino)propanoic Acid as a Ligand.