Direct C—H Arylation of 3‐Methoxythiophene Catalyzed by Pd. Application to a more Efficient Synthesis of π‐Alkoxy‐oligothiophene Derivatives.

Borghese, A.; Geldhof, Geoffroy; Antoine, Luc

doi:10.1002/chin.200714124

Cited by 2 publications

(4 citation statements)

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“…The reaction takes place between 2-bromothiophene and EDOT and it is catalyzed by Pd(OAc) 2 or Pd(Cl) 2 . This approach provides a simple way for the synthesis of oligothiophene series [ 71 ].…”

Section: Trimer Structuresmentioning

confidence: 99%

“…It is known that alkoxy chains increase the solubility and improve the electronic properties of trimers and, therefore, their presence is ubiquitous in the literature. Typically, two O-connected alkyl chains (one per lateral unit) are found in 3 and 3″ [ 71 , 283 , 284 , 285 , 286 ] or in 4 and 4″ position of the trimer ( Scheme 16 , I) [ 287 , 288 , 289 , 290 , 291 , 292 , 293 , 294 ]. Besides, structures with one [ 295 , 296 ] or two [ 297 , 298 ] alkoxy groups on the central thiophene, in 3′ and 4′ position, were synthesized.…”

Section: Trimer Structuresmentioning

confidence: 99%

“…afforded an asymmetric trimer with the aldehyde attached to position 4 of a lateral unit [ 278 ]. Trimers with two aldehyde groups were also prepared, in position 3′ and 4′ on the central unit [ 242 ], or in position 3 and 3″ on the lateral units [ 71 ]. The presence of an aldehyde group connected to the thiophene ring is of great advantage for the functionalization of trimers.…”

Section: Trimer Structuresmentioning

confidence: 99%

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Thiophene-Based Trimers and Their Bioapplications: An Overview

et al. 2021

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Certainly, the success of polythiophenes is due in the first place to their outstanding electronic properties and superior processability. Nevertheless, there are additional reasons that contribute to arouse the scientific interest around these materials. Among these, the large variety of chemical modifications that is possible to perform on the thiophene ring is a precious aspect. In particular, a turning point was marked by the diffusion of synthetic strategies for the preparation of terthiophenes: the vast richness of approaches today available for the easy customization of these structures allows the finetuning of their chemical, physical, and optical properties. Therefore, terthiophene derivatives have become an extremely versatile class of compounds both for direct application or for the preparation of electronic functional polymers. Moreover, their biocompatibility and ease of functionalization make them appealing for biology and medical research, as it testifies to the blossoming of studies in these fields in which they are involved. It is thus with the willingness to guide the reader through all the possibilities offered by these structures that this review elucidates the synthetic methods and describes the full chemical variety of terthiophenes and their derivatives. In the final part, an in-depth presentation of their numerous bioapplications intends to provide a complete picture of the state of the art.

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Section: Trimer Structuresmentioning

confidence: 99%

Section: Trimer Structuresmentioning

confidence: 99%

Section: Trimer Structuresmentioning

confidence: 99%

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Thiophene-Based Trimers and Their Bioapplications: An Overview

et al. 2021

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“…Several reports about regioselective Suzuki coupling of dibromothiophene are available in literature [ 14 , 15 ]. Palladium catalyzed coupling of 2,5-dibromothiophene has been reported and the yield of obtained product was low (29%) [ 16 ]. Synthesis of 2,5-diheteroarylated thiophenes from 2,5-dibromo thiophene derivatives has been reported in good yield [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Palladium(0) catalyzed Suzuki cross-coupling reaction of 2,5-dibromo-3-methylthiophene: selectivity, characterization, DFT studies and their biological evaluations

Zubaır

Rasool

Mahmood

et al. 2018

Chemistry Central Journal

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Thiophene derivatives have shown versatile pharmacological activities. The Suzuki reaction proved a convenient method for C–C bond formations in organic molecules. In the present research work novel derivatives of 2,5-dibromo-3-methylthiophene (3a–k and 3l–p) has been synthesized, via Suzuki coupling reaction in low to moderate yields. A wide range of functional groups were well tolerated in reaction. Density functional theory investigations on all synthesized derivatives (3a–3p) were performed in order to explore the structural properties. The pharmaceutical potential of synthesized compounds was investigated through various bioassays (antioxidant, antibacterial, antiurease activities). The compounds 3l, 3g, 3j, showed excellent antioxidant activity (86.0, 82.0, 81.3%), respectively by scavenging DPPH. Synthesized compounds showed promising antibacterial activity against tested strains. 3b, 3k, 3a, 3d and 3j showed potential antiurease activity with 67.7, 64.2, 58.8, 54.7 and 52.1% inhibition at 50 µg/ml. Results indicated that synthesized molecules could be a potential source of pharmaceutical agents.Electronic supplementary materialThe online version of this article (10.1186/s13065-018-0404-7) contains supplementary material, which is available to authorized users.

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Direct C—H Arylation of 3‐Methoxythiophene Catalyzed by Pd. Application to a more Efficient Synthesis of π‐Alkoxy‐oligothiophene Derivatives.

Abstract: ChemInform 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.

Cited by 2 publications

References 1 publication

Thiophene-Based Trimers and Their Bioapplications: An Overview

Thiophene-Based Trimers and Their Bioapplications: An Overview

Palladium(0) catalyzed Suzuki cross-coupling reaction of 2,5-dibromo-3-methylthiophene: selectivity, characterization, DFT studies and their biological evaluations

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