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Toward Asymmetric Synthesis of Pentaorganosilicates

Introducing chiral silicon centers was explored for the asymmetric Rh-catalyzed cyclization of dihydrosilanes to enantiomerically enriched spirosilanes as targets to enable access to enantiostable pentacoordinate silicates. The steric rigidity required in such systems demands the presence of two naphthyl or benzo[b]thiophene groups. The synthetic approach to the expanded spirosilanes extends Takai?s method (Kuninobu et al. in Angew Chem Int Ed 52(5):1520?1522, 2013) for the synthesis of spirosilabifluorenes in which both a Si?H and a C?H bond of a dihydrosilane are activated by a rhodium catalyst. The expanded dihydrosilanes were obtained from halogenated aromatic precursors. Their asymmetric cyclization to the spirosilanes were conducted with [Rh(cod)Cl]2 in the presence of the chiral bidentate phosphane ligands (R)-BINAP, (R)-MeO-BIPHEP, and (R)-SEGPHOS, including derivatives with P-(3,5-t-Bu-4-MeO)-phenyl (DTBM) groups. The highest enantiomeric excess of 84% was obtained for 11,11?-spirobi[benzo[b]-naphtho[2,1-d]silole] with the DTBM-SEGPHOS ligand.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Synthesis of 3-bromosubstituted 2-arylbornylenes by cross-coupling

A catalyzed reaction of aryl group addition to bornene system is reported. This reaction is interesting for designing new chiral ligands based on camphor. Nauka/Interperiodica 2007.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Benzo[b]thiophene-fused boron and silicon ladder acenes

Synthetic routes to three new heteroacene compounds in which two benzo[b]thienyl units are bridged by dimethylsilyl and/or mesitylboryl units are described. In the Si/Si and Si/B compounds 1-syn and 3-syn, respectively, the sulfur atoms of the flanking benzo[b]thiophenes are disposed in meta positions on the central six-membered heterocycle, while in the B/B compound 4-anti, they are para to each other; the reasons for this lie in the synthetic method employed to prepare 4-anti. All three compounds were crystallographically characterized and their photophysical properties examined. A comprehensive examination of their photophysical properties shows that they are weakly absorbing and fluorescing materials, with the diborin derivative 4-anti exhibiting the most red-shifted absorption maxima and largest fluorescence quantum yield.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Aromatic and Antiaromatic Pathways in Triphyrin(2.1.1) Annelated with Benzo[b]heterocycles

Understanding of the aromatic properties and magnetically induced current densities of highly conjugated chromophores is important when designing molecules with strongly delocalized electronic structure. Linear extension of the triphyrin(2.1.1) skeleton with an annelated benzo[b]heterocycle fragment modifies the aromatic character by extending the electron delocalization pathway. Two-electron reduction leads to an antiaromatic triphyrin(2.1.1) ring and an aromatic benzo[b]heterocycle subunit. Current-density calculations provide detailed information about the observed pathways and their strengths.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Can You Really Do Chemisty Experiments About 2,3-Dibromobenzo[b]thiophene

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A one-pot synthesis of hindered 2,3-diarylbenzo[b]thiophenes via suzuki reaction

Palladium-catalysed cross-coupling of 2,3-dibromobenzo [b]thiophene with phenylboronic acids bearing two ortho substituents have been developed and used for the synthesis of sterically hindered 2,3-diarylbenzo[b]thiophenes.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Triphenylene-Benzofuran/Benzothiophene/Benzoselenophene Compounds With Substituents Joining To Form Fused Rings

Compounds comprising a triphenylene moiety and a benzo- or dibenzo-moiety are provided. In particular, the benzo- or dibenzo-moiety has a fused substituent. These compounds may be used in organic light emitting devices, particularly in combination with yellow, orange and red emitters, to provide devices with improved properties.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Metal-catalyzed direct arylation of 1,2-azoles

Over the last 20 years, there has been significant progress in the direct CH (het)arylation chemistry of a wide variety of (het)arenes. Herein, the application of direct CH arylation on the 1,2-azoles: pyrazoles, isothiazoles, and isoxazoles and their annulated analogues is reviewed starting from the first arylation methods on 1,2-azoles until 2018.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Benzothiophene or benzofuran bridges in diaryl ethenes: Two-step access by Pd-catalyzed C-H activation and theoretical/experimental studies on their photoreactivity

A series of terarylenes incorporating benzothiophene (BT)/benzofuran (BF) as the central ethene unit was synthesised by using sequential Pd-catalysed C – H activation reactions. This new methodology allows the easy modification of the nature of the pendant heteroarene groups. Diaryl ethene (DAE) derivatives with thiophene, thiazole, pyrrole, isoxazole and pyrazole rings were prepared. A large number of asymmetrical DAEs are easily accessible by this new method in both the BT and BF series. The study of their photochromic properties in solution revealed that the nature of the heteroarene and of the central unit drastically modify their photochromic behaviour. TD-DFT calculations were performed to assess the nature of the relevant excited states.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Palladium-catalyzed synthesis of isoindoloquinazolinones via dicarbonylation of 1,2-dibromoarenes

A convenient procedure for the carbonylative synthesis of isoindoloquinazolinones has been developed. Using 1,2-dibromobenzenes and 2-aminobenzyl amine as substrates and palladium as the catalyst, the desired products were isolated in moderate to good yields with the installation of two molecules of carbon monoxide. Notably, this is the first example of carbonylative synthesis of batracylin analogues. This journal is the Partner Organisations 2014.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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The first five-membered-heterocycle-fused subphthalocyanine analogues: Chiral Tri(Benzo [b] Thiopheno)subporphyrazines

Two tri(benzo[b]thiopheno)subporphyrazine regioisomers with C3 and C1 molecular symmetry have been isolated from the cyclotrimerization of benzo[b]thiophene-2,3-dicarbonitrile as the first five-membered-heterocycle-fused subphthalocyanine analogues. Optical resolution of both regioisomers was achieved by using a chiral HPLC technique, affording the first chiral subphthalocyanine analogues.

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Reference£º
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem