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Elongated phosphoranes by C-C coupling of haloaroylmethylidene-triphenylphosphoranes: Synthesis and applications

Haloaroylmethylidenephosphoranes 3 can be subjected to Pd(o) mediated C-C coupling reactions to yield diaryl-, arylhetaryl-, dihetaryl, arylethenylaryl/hetaryl- and arylethynylaryl/hetaryl-carbonylmethylidenephosphoranes 4-9. Suzuki-Kumada reactions can also be run in a one-step procedure from (haloaroylmethyl)triphenylphosphonium bromides 2. Compounds 4-9 are air-stable phosphoranes which undergo formal Wittig-olefination reactions with aldehydes 10 under benzoic acid catalysis. C-C coupling reaction and Wittig olefination can also be performed in a one-step procedure. Preliminary experiments have been performed to carry out the synthesis on a solid support. Applications to the chain elongation and functionalisation of the chain terminus in a C-7 substituted estra-1,3,5(10)-triene 14 and a C-16 substituted estra-1,3,5(10),6-tetraene 12 are shown.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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A Heteroarylamine Library: Indium-Catalyzed Nucleophilic Aromatic Substitution of Alkoxyheteroarenes with Amines

Under indium Lewis acid catalysis, electron-rich five-membered heteroaryl electrophiles fused with/without a benzene ring were found to couple with amines to produce heteroarylamines with broad structural diversity. The heteroarylamine formation proceeds through the cleavage of a heteroaryl?OMe bond by the nucleophilic attack of the amine based on the nucleophilic aromatic substitution (SNAr) reaction. In contrast to the corresponding traditional SNAr amination, the present SNAr-based heteroaryl amination can be performed without relying on both heteroaryl electrophiles with electron-withdrawing groups and nucleophilicity-enhanced metal amides. High compatibility towards the functional groups such as NO2, Br, I, CF3, CN, CO2Et, pyridyl, thiazolyl, C=C, and OH groups was observed, thus showing the practicality and reliability of this method. Mechanistic studies indicated that a carbon?indium bond is likely to be formed on the heteroaryl ring during the process. (Figure presented.).

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

Some scientific research about 2-Bromobenzo[b]thiophene

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Room-temperature hydrodehalogenation of halogenated heteropentalenes with one or two heteroatoms

The pair NaBH4-TMEDA as a hydride source and catalytic PdCl 2(dppf) in THF prove to be an efficient system for the hydrodehalogenation of bromo(chloro)-heteropentalenes with one or two heteroatoms, while Pd(OAc)2/PPh3 is able to reduce reactive haloheteropentalenes, and PdCl2(tbpf) allows the removal of the 2-chlorine from a thiophene ring. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene, and nitrile substituents and also showing good efficiency in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Mononuclear piano-stool iron 2-ethynylbenzo[b]thiophene complex: crystal structure and reversible oxidation studied by spectro-electrochemical and DFT methods

A mononuclear iron complex with 2-ethynylbenzo[b]thiophene C-coordinated to the (eta5-Cp*)(eta2-dppe)Fe (Cp*?=?pentamethylcyclopentadienyl, dppe?=?1,2-diphenylphosphinoethane) framework (1) was prepared and characterized by 1H NMR, elemental analysis, and single crystal X-ray diffraction. The redox behavior of 1 was investigated by voltammetric methods and anodic spectroelectrochemistry in the UV?vis-NIR-IR region and compared with reference complexes including 2-ferrocenylbenzo[b]thiophene (2) and the 2-ethynylpyridine derivative of 1. The spin density distribution along the linear molecular backbone in 1+ was analyzed by DFT (BLYP35) and TDDFT calculations of a truncated model complex. The combined experimental and theoretical results revealed an important role of the ethynylene linker in determining the redox properties of this family of complexes and participation of the 2-ethynylbenzo[b]thiophene framework in the largely iron-based anodic electron transfer.

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Benzothiophene – Wikipedia,
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Modulation of aggregation-induced emission and electroluminescence of silole derivatives by a covalent bonding pattern

The deciphering of structure-property relationships is of high importance to rational design of functional molecules and to explore their potential applications. In this work, a series of silole derivatives substituted with benzo[b]thiophene (BT) at the 2,5-positions of the silole ring are synthesized and characterized. The experimental investigation reveals that the covalent bonding through the 2-position of BT (2-BT) with silole ring allows a better conjugation of the backbone than that achieved though the 5-position of BT (5-BT), and results in totally different emission behaviors. The silole derivatives with 5-BT groups are weakly fluorescent in solutions, but are induced to emit intensely in aggregates, presenting excellent aggregation-induced emission (AIE) characteristics. Those with 2-BT groups can fluoresce more strongly in solutions, but no obvious emission enhancements are found in aggregates, suggesting they are not AIE-active. Theoretical calculations disclose that the good conjugation lowers the rotational motions of BT groups, which enables the molecules to emit more efficiently in solutions. But the well-conjugated planar backbone is prone to form strong intermoelcular interactions in aggregates, which decreases the emission efficiency. Non-doped organic light-emitting diodes (OLEDs) are fabricated by using these siloles as emitters. AIE-active silole derivatives show much better elecroluminescence properties than those without the AIE characterisic, demonstrating the advantage of AIE-active emitters in OLED applications. Stay connected! Connecting benzo[b]thiophene with a silole ring through its 2- or 5-position furnishes silole derivatives with totally different photoluminescence and electroluminescence properties (see figure).

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alpha-Arylation/Heteroarylation of Chiral alpha-Aminomethyltrifluoroborates by Synergistic Iridium Photoredox/Nickel Cross-Coupling Catalysis

Direct access to complex, enantiopure benzylamine architectures using a synergistic iridium photoredox/nickel cross-coupling dual catalysis strategy has been developed. New C(sp3)-C(sp2) bonds are forged starting from abundant and inexpensive natural amino acids.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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AMINOISOXAZOLINE COMPOUNDS AS AGONISTS OF ALPHA7-NICOTINIC ACETYLCHOLINE RECEPTORS

The present invention relates to novel aminoisoxazoline compounds, and pharmaceutical compositions of the same, that are suitable as agonists or partial agonists of alpha7-nAChR, and methods of preparing these compounds and compositions, and the use of these compounds and compositions in methods of maintaining, treating and/or improving cognitive function. In particular, methods of administering the compound or composition to a patient in need thereof, for example a patient with a cognitive deficiency and/or a desire to enhance cognitive function, that may derive a benefit therefrom.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Single-Electron Transmetalation: Protecting-Group-Independent Synthesis of Secondary Benzylic Alcohol Derivatives via Photoredox/Nickel Dual Catalysis

Protecting-group-independent cross-coupling of alpha-alkoxyalkyl- and alpha-acyloxyalkyltrifluoroborates with aryl and heteroaryl bromides is achieved through application of photoredox/nickel dual catalysis. Reactions occur under exceptionally mild conditions, with outstanding functional group compatibility and excellent observed tolerance of heteroarenes. This method offers expedient access to protected secondary benzylic alcohol motifs bearing benzyl, pivaloyl, and N,N-diisopropylcarbamoyl protecting groups.

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Benzothiophene – Wikipedia,
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Potential-driven chirality manifestations and impressive enantioselectivity by inherently chiral electroactive organic films

The typical design of chiral electroactive materials involves attaching chiral pendants to an electroactive polyconjugated backbone and generally results in modest chirality manifestations. Discussed herein are electroactive chiral poly-heterocycles, where chirality is not external to the electroactive backbone but inherent to it, and results from a torsion generated by the periodic presence of atropisomeric, conjugatively active biheteroaromatic scaffolds, (3,3-bithianaphthene). As the stereogenic element coincides with the electroactive one, films of impressive chiroptical activity and outstanding enantiodiscrimination properties are obtained. Moreover, chirality manifestations can be finely and reversibly tuned by the electric potential, as progressive injection of holes forces the two thianaphthene rings to co-planarize to favor delocalization. Such deformations, revealed by CD spectroelectrochemistry, are elastic and reversible, thus suggesting a breathing system. A jolt upon recognition: Torsion in the electroactive backbone endows poly-heterocycle films with high chiroptical activity, which is reversibly tunable by the electric potential, and outstanding enantiorecognition capability with about 100 mV between two enantiomeric ferrocenyl amino probes, in any order, in alternating sequences, and as a racemate.

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Benzothiophene – Wikipedia,
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Selective Acylation of Aryl- A nd Heteroarylmagnesium Reagents with Esters in Continuous Flow

A selective acylation of readily accessible organomagnesium reagents with commercially available esters proceeds at convenient temperatures and short residence times in continuous flow. Flow conditions allow us to prevent premature collapse of the hemiacetal intermediates despite noncryogenic conditions, thus furnishing ketones in good yields. Throughout, the coordinating ability of the ester and/or Grignard was crucial for the reaction outcome. This was leveraged by the obtention of several bisaryl ketones using 2-hydroxy ester derivatives as substrates.

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Benzothiophene – Wikipedia,
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