Programmed Site‐Selective Palladium‐Catalyzed Arylation of Thieno[3,2<i>‐b</i>]thiophene

Vuong, Thi Minh Ha; Villemin, Didier; Hung-Huy, Nguyen; Le, Tin Thanh; Dang, Tung T.; Nguyen, Hien

doi:10.1002/asia.201700562

Cited by 6 publications

(3 citation statements)

References 41 publications

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“…For the compounds 3 and 11 , general conditions of Suzuki coupling were employed starting from commercially available or easily prepared aryl boronic acids (See SI for details). The derivative 4 was obtained by CH activation strategy [47] as reported in literature. In all cases, coumarins were isolated in satisfactory yields.…”

Section: Resultsmentioning

confidence: 99%

Tailored Coumarin Dyes for Photoredox Catalysis: Calculation, Synthesis, and Electronic Properties

et al. 2020

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High level time‐dependent density functional theory (TD‐DFT) computational modeling of coumarin dyes has been exploited for guiding the design of effective photocatalysts (PCs). A library of coumarins were investigated from the theoretical point of view and photophysical/electrochemical properties (absorption and emission spectra, E00, oxidation and reduction potentials) were evaluated. Comparison with literature values reported for a few candidates has been used for assessing the level of theory. On the basis of the results obtained, new strongly reducing PCs [Eox(PC.+/PC*)=−2.1 – −2.0 V vs SCE] were discovered. Through the computational study of structure‐properties relationships, a number of coumarins derivatives have been synthesized and evaluated in the pinacol coupling of aldehydes as the model reaction. The new organic photoredox catalysts show experimental photophysical and electrochemical data in accordance with the ones predicted by calculation, with excited state reduction potentials surpassing those of highly reducing transition metal‐based PCs. A careful investigation of their behavior as PC has revealed crucial issues that need to be taken into consideration in the general photoredox catalysis, shedding light on the use of these PC in the pinacol, as well as, in other photoredox reactions.

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Section: Resultsmentioning

confidence: 99%

Tailored Coumarin Dyes for Photoredox Catalysis: Calculation, Synthesis, and Electronic Properties

et al. 2020

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“…The reported procedure has been modified for gem-1,1-dibromo-2,2-dithienylethene and phenylboronic acid to give DPDTE with a 55% isolated yield. The palladium-catalyzed C-H functionalization of the thiophene and thienothiophene have been optimized by Doucet [20] and our group [21]. This ligand-free catalytic system consisted of only two components Pd(OAc) 2 and KOAc with DMAc as solvent, can be applied to various thiophene derivatives with good functional group tolerance.…”

Section: Synthesismentioning

confidence: 99%

Palladium-Catalyzed Direct Mono- and Diarylation of Diphenydithienylethenes: A Useful Method for Enhancing Fluorescence Intensity and Aggregation-Induced Emission

Phan

et al. 2021

Molbank

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In this study we report efficient method for the syntheses of mono- and diarylated diphenyldithienylethene (DPDTE) via a palladium-catalyzed C–H arylation reaction. These new derivatives showed amplified luminescent properties thanks to a change in polarity, particularly in the presence of an electron-withdrawing groups (EWG). Moreover, the arylated DPDTEs showed dual-emissive phenomena, including fluorescence in organic solvents and aggregation-induced emission.

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“…. 117 It was seen that when the C2 position was substituted with an aryl having an electron-withdrawing nature, C3 of the same part of the ring can be sequentially arylated due to the increased acidity of the C−H bond, providing a C2 → C3 sequence, 214. This hypothesis was validated by the comparatively downfield shifts of C3 protons compared to C5 protons.…”

Section: Sequential C-arylation Of 55-fused Heteroarenesmentioning

confidence: 99%

Strategic Advances in Sequential C-Arylations of Heteroarenes

et al. 2020

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Sequence-specific C-arylation strategies have important applications in medicinal and material research. These strategies allow C–C bond formations in a regioselective manner to synthesize large molecular libraries for studying structure–activity profiles. The past decade has seen the development of single C–C bond forming reactions using various transition-metal catalysts, cryogenic metalation strategies, and metal-free methods. Sequential arylations of heterocycles allow for the formation of multiaryl derivatives and are a preferred choice over de novo synthetic routes. This perspective sheds light on recent strategic advances to develop various sequential synthetic routes for the multiarylation of heteroarenes. This perspective addresses many challenges in optimizing sequential routes with respect to catalysts, reaction parameters, and various strategies adopted to obtain diversely arylated products.

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Programmed Site‐Selective Palladium‐Catalyzed Arylation of Thieno[3,2‐b]thiophene

Cited by 6 publications

References 41 publications

Tailored Coumarin Dyes for Photoredox Catalysis: Calculation, Synthesis, and Electronic Properties

Tailored Coumarin Dyes for Photoredox Catalysis: Calculation, Synthesis, and Electronic Properties

Palladium-Catalyzed Direct Mono- and Diarylation of Diphenydithienylethenes: A Useful Method for Enhancing Fluorescence Intensity and Aggregation-Induced Emission

Strategic Advances in Sequential C-Arylations of Heteroarenes

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