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The synthesis of highly substituted 1,3-dienes from the coupling of vinyl bromides with vinyl triflates is reported for the first time. The coupling is catalyzed by a combination of (5,5?-bis(trifluoromethyl)-2,2?-bipyridine)NiBr2 and (1,3-bis(diphenylphosphino)propane)PdCl2 in the presence of a zinc reductant. This method affords tetra- and penta-substituted 1,3-dienes that would otherwise be difficult to access and tolerates electron-rich and -poor substituents, heterocycles, an aryl bromide, and a pinacol boronate ester. Mechanistically, the reaction appears to proceed by an unusual zinc-mediated transfer of a vinyl group between the nickel and palladium centers.

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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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3-Oxo-2,3-dihydrobenzo[b]furans, -thiophenes and -selenophenes 1a-c afforded the bromo-aldehydes 2 under Vilsmeier-Haack-Arnold conditions. Palladium-catalysed aryl-aryl coupling of 2 with o-formyl-phenylboronic acid allowed the formation of dialdehydes 3 which underwent McMurry cyclisation or pinacol condensation to yield polycyclic aromatic derivatives 4 or the dihydroxylated compounds 5.

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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Hemithioindigo (HTI) photoswitches have a tremendous potential for biological and supramolecular applications due to their absorptions in the visible-light region in conjunction with ultrafast photoisomerization and high thermal bistability. Rational tailoring of the photophysical properties for a specific application is the key to exploit the full potential of HTIs as photoswitching tools. Herein we use time-resolved absorption spectroscopy and Hammett analysis to discover an unexpected principal limit to the photoisomerization rate for donor-substituted HTIs. By using stationary absorption and fluorescence measurements in combination with theoretical investigations, we offer a detailed mechanistic explanation for the observed rate limit. An alternative way of approaching and possibly even exceeding the maximum rate by multiple donor substitution is demonstrated, which give access to the fastest HTI photoswitch reported to date. An unexpected principal limit to the photoisomerization rate for donor-substituted hemithioindigos (HTIs; see figure) has been discovered; this provides a quantitative estimate for the highest possible photoisomerization rate. A mechanistic explanation for the observed limit is offered together with an alternative way of approaching the maximum rate by multiple donor substitution. This approach gave access to the fastest HTI photoswitch reported to date.

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Reference:
Benzothiophene – Wikipedia,
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In heterogeneous catalysis, catalysts provide a surface to which reactants bind in a process of adsorption. The reactant in an enzyme-catalyzed reaction is called a substrate. Formula: C8H6OS, C8H6OS. A document type is Article, introducing its new discovery., Formula: C8H6OS

13C NMR spectra of the title compounds have been fully assigned.The results have been compared with those relative to other chalcogenated compounds, such as anisole, phenyl benzoate, benzofuran,… and their analogs.In chalcogenochromones and -coumarines, the heteroatom lone pair delocalization spreads to some extent over the heterocyclic part of the molecules, while in chalcogenochromanones and -indoxyles, it only extends to the homocycle.This electronic effect seems also to affect the heavy atom effect exhibited by Te-containing compounds.

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Reference:
Benzothiophene – Wikipedia,
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The present invention encompasses compounds of the formula (I)(I) wherein the variables are defined herein which are suitable for the modulation of RORgamma and the treatment of diseases related to the modulation of RORgamma. The present invention also encompasses processes of making compounds of formula (I) and pharmaceutical preparations containing them.

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Benzothiophene – Wikipedia,
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gamma-Radiolysis of aqueous benzothiophene solutions saturated with N2O has been studied.In the absence of other reagents, the only products detected are 2- and 3-hydroxybenzothiophene and their corresponding lactonic and ketonic tautomers and a small amount of dimeric species.In the presence of potassium hexacyanoferrate or sodium hydroxide, however, products attributable to hydroxylation at all six available carbon sites are detected and dimer formation is reduced.Analysis of the experimental data suggests that both benzothiophene and its hydroxylation products are efficient scavengers for the radiation-produced OH radicals and that the initial yield of hydroxylation products is equal to that of hydroxyl radicals.Consistent with the electrophilic characteristics of the OH radical, k(OH+C8H6S):k(OH+C8H5SOH)=0.5+/-0.1.All six available carbon sites are capable of forming OH adducts, but the radicals formed by addition to the 4, 5, 6, and 7 positions tend to revert to the original compound or its ion in a neutral or acidic medium.In the case of the adducts formed by addition to the thiophene ring, on the other hand, the 3 position is seen to be favored, possibly as the result of the preservation of the aromatic benzene resonance structure.

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Reference:
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A new class of bidirectionally quantitative photoswitches based on the hemithioindigo (HTI) scaffold is reported. Incorporation of a pyrrole hydrogen-bond donor leads to a bathochromic shift allowing for quantitative bidirectional isomerization. Additionally, extending conjugation from the electron-rich pyrrole results in quantitative visible-light photoswitches, as well as photoswitches that isomerize with red and near-infrared light. The presence of the hydrogen bond leading to the observed redshift is supported by computational and spectroscopic evidence.

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Benzothiophene – Wikipedia,
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The reaction of alkyl 4-(2-acetylhydrazino)-2-methyl-3- thiophenecarboxylates with 3-methylbutan-2-one was carried out under the Fischer reaction conditions. The influence of Lewis acids and solvents on the process was studied. A convenient method for the synthesis of thieno [3.2-b]pyrrolenine derivatives was proposed.

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A reinvestigation of the reaction of the dihydrothiophenes (1a, b) with thionyl chloride confirmed that the sulphines (2) are the products obtained, the structure of (2a) being ascertained by X-ray diffraction analysis of its Diels-Alder adduct (3a): the same reaction on dihydrothiophene (6) produced the corresponding sulphine (7).

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Benzothiophene – Wikipedia,
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An organocatalytic asymmetric formal aza-[3+3]cycloaddition of readily available N-Tosyl-3-aminobenzofuran with alpha,beta-unsaturated aldehydes was developed for the first time. This method enables the facile synthesis of biologically active and synthetically challenging polysubstituted fused benzofuran derivatives bearing two stereocenters in high yields with excellent diastereo-, and enantioselectivity (up to >20 : 1 dr, and >99% ee). (Figure presented.).

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Reference:
Benzothiophene – Wikipedia,
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