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Rh(iii)-Catalyzed oxidative C-H/C-H cross-coupling between benzaldehydes and thiophenes has been accomplished for the first time. In such reactions, transient directing ligands (TDLs) can not only promote ortho-C-H activation, but can also control the chemoselectivity through a suitable combination of different solvents.

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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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The development of a rational strategy to achieve the complete regioselectivity and the capability to switch regioselectivity is an appealing, yet challenging, puzzle in transition-metal-catalyzed oxidative Ar-H/Ar-H cross-coupling. Disclosed herein is an iridium-catalyzed C2/C4 regioselective C-H heteroarylation of indoles with the help of a pivaloyl group at the C3 position. The judicious choice of the catalytic systems allows the C2-heteroarylation of indole via a concerted metalation-deprotonation (CMD) process and the C4-heteroarylation via a trimolecular electrophilic substitution (SE3) pathway. The oxidants Cu(OAc)2·H2O and Ag2O are demonstrated to play a vital role in the C2/C4 regioselectivity. In this Article, a heteroaryl-Ir(III)-heteroaryl complex prior to reductive elimination is successfully isolated and characterized, which represents the first example of capturing the bis(hetero)aryl metallic intermediate in oxidative Ar-H/Ar-H cross-coupling. The regiodivergent heteroarylation of indoles developed herein provides an opportunity to rapidly assemble diverse C4- and C2-heteroarylated indoles.

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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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The reactant in an enzyme-catalyzed reaction is called a substrate. Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction. Quality Control of 5-Bromobenzothiophene, such as the rate of change in the concentration of reactants or products with time.In a article, mentioned the application of 4923-87-9, Name is 5-Bromobenzothiophene, molecular formula is C8H5BrS

This report demonstrates the possibility of a nickel-catalyzed difunctionalization of unactivated alkenes initiated by an unstabilized enolate nucleophile. The process tolerates a diverse range of electrophiles, including aryl, heteroaryl, alkenyl, and amino electrophiles. An electron-deficient phosphine ligand and a tetrabutylammonium salt additive were crucial for promoting efficient vicinal difunctionalization.

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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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4923-87-9, 5-Bromobenzothiophene is a benzothiophene compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,4923-87-9

Example 52 Preparation of (+)-5-benzo[b]thiophen-5-yl-8-methoxy-2-methyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, maleate salt and (-)-5-benzo[b]thiophen-5-yl-8-methoxy-2-methyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, maleate salt Step A: To a solution of 5-bromobenzo[b]thiophene (5.0 g, 23.5 mmol) in N,N-dimethylformamide (50 mL) at room temperature were added tri-o-tolylphosphine (0.64 g, 2.1 mmol) and triethylamine (9.9 mL, 70.4 mmol). The reaction mixture was degreased with argon and then ethyl acrylate (7.7 mL, 70.4 mmol) and tris(dibenzylideneacetone)dipalladium(0) (0.65 g, 0.7 mmol) were added to it. The resultant solution was degreased with argon and then heated at 100 C. overnight. The reaction solution was then cooled to room temperature, diluted with ethyl acetate, washed with water (2×), saturated ammonium chloride and brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product obtained was purified by flash column chromatography (95:5 to 93:7 hexanes/ethyl acetate) to give the desired product (2.5 g, 46%) as a light yellow oil: 1H NMR (CDCl3, 500 MHz) delta 7.94 (d, J=1.5 Hz, 1H), 7.87 (d, J=8.5 Hz, 1H), 7.81 (d, J=16.0 Hz, 1H), 7.54 (dd, J=8.4 and 1.6 Hz, 1H), 7.49 (d, J=5.4 Hz, 1H), 7.36 (d, J=5.4 Hz, 1H), 6.50 (d, J=15.9 Hz, 1H), 4.28 (q, J==7.2 Hz, 2H), 1.35 (t, J=7.2 Hz, 3H).

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Reference:
Patent; AMR Technology, Inc.; US2007/21408; (2007); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4923-87-9,5-Bromobenzothiophene,as a common compound, the synthetic route is as follows.

In DMF (500 parts), 5-bromobenzo[b]thiophene (20 parts), phenylboronic acid (13.7 parts),Tripotassium phosphate (113 parts) and hydrazine (triphenylphosphine) palladium (3.0 parts) were mixed, and stirred at 70 C for 6 hours under a nitrogen atmosphere.After cooling the obtained reaction liquid to room temperature, water (500 parts) was added, and the solid fraction was separated by filtration.The obtained solid fraction was dried by washing with water and acetone to obtain 5-phenylbenzo[b]thiophene (13.3 parts, yield 67%).

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Reference:
Patent; NIPPON KAYAKU KABUSHIKI KAISHA; NIIMI, KAZUKI; TONE, YUSUKE; YAKUSHIJI, HIDENORI; (67 pag.)TW2018/31491; (2018); A;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

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(A) To a cooled (-10 C. to 5 C.) solution of diisopropylamine (422 g, 4.17 mol) in anhydrous THF (4.0 L) was added n-butyllithium (1517 mL of 2.5 M in hexane, 3.79 mol) in drop-wise fashion over a period of 1.5 h under an inert atmosphere of nitrogen. Upon completion of the addition, the reaction solution was stirred at -10 C. to 0 C. for an additional 30 min, and then cooled to -78 C. A solution of 5-bromobenzo[b]thiophene (670 g, 3.16 mol) and TMSCl (512 g, 4.74 mol) in THF (3.4 L) was added in drop-wise fashion and the resulting reaction mixture was stirred at -78 C. After completion of the reaction, as judged by HPLC analysis, aq. NH4Cl solution (5% w/w, 2 L) was added in drop-wise fashion into the reaction mixture while still under a nitrogen atmosphere and maintaining a temperature between -78 C. and -65 C. The mixture was then allowed to warm to rt and the aqueous phase was removed. Water (2 L) was added to the organic phase and after stirring at room temperature for 15 min, the aqueous phase was removed. The combined aqueous layers were back-extracted with EtOAc (2 L), and the combined organic extracts were washed with sat.d aq. NaCl (2 L), dried (Na2SO4) and concentrated under reduced pressure to provide (5-bromobenzo[b]thiophen-2-yl)trimethylsilane (867 g, purity: 90.0 LCAP) as a light yellow liquid. 1H NMR (CDCl3) delta 7.93 (d, J=1.5 Hz, 1H), 7.72 (d, J=8.4 Hz, 1H), 7.39 (d, J=8.4 Hz, 1H), 7.36 (s, 1H), 0.37 (s, 9H); LC/MS (APCI+) m/z 283.9 [M]+.

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Reference:
Patent; Janssen Pharmaceutica NV; Liang, Yin; Demarest, Keith T.; (109 pag.)US2017/290800; (2017); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

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(C) To a solution of 5-bromo-1-benzothiophene (12 g, 56.31 mmol) in dry THF (300 mL) under an inert atmosphere was added isopropyl magnesium chloride- lithium chloride complex (1.3 M in THF; 150 mL, 195 mmol) in drop-wise fashion, and the resultant solution was stirred at rt, overnight. DMF (30 mL) was then added in drop-wise fashion and the resultant solution was stirred at rt for 30 min. Water (500 mL) was added and the resulting solution was extracted with ethyl acetate (3 x 500 mL). The combined organic extracts were concentrated under reduced pressure and the resultant residue was purified by silica gel chromatography (0-2% EtOAC/ petroleum ether) to provide benzo[b]thiophene-5-carbaldehyde (6.9 g, 68 %) as a yellow solid. 1H NMR (DMSO-d6) G 10.12 (s, 1H), 8.32 (s, 1H), 8.01 (d, J = 8.4 Hz, 1H), 7.86 – 7.89 (m, 1H), 7.57 – 7.61 (m, 1H), 7.47 – 7.50 (m, 1H).

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Reference:
Patent; JANSSEN PHARMACEUTICA NV; KUO, Gee-Hong; PLAYER, Mark R.; YANG, Shyh-Ming; ZHANG, Yue-Mie; HUANG, Hui; (260 pag.)WO2016/57731; (2016); A1;,
Benzothiophene – Wikipedia
Benzothiophene | C8H6S – PubChem

 

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The purpose of the present invention is to provide a method for easily producing a fluorine-containing (cyclo)alkenyl zinc halide compound at low cost. The present invention provides a method for producing a fluorine-containing (cyclo)alkenyl zinc halide compound represented by formula (1) (wherein A1 represents a perfluoroalkyl group having 1-12 carbon atoms, or a fluorine atom; A2 represents a fluorine atom or a hydrogen atom; A3 represents a fluorine atom or a hydrogen atom, or alternatively A3 and A1 or A2 may combine together to form a perfluoroalkylene chain having 1-12 carbon atoms; and X’ represents a halogen atom), which comprises a step wherein a fluorine-containing olefin represented by formula (2) (wherein X” represents a fluorine atom or a chlorine atom; and the other symbols are as defined above) is reacted with a zinc halide represented by formula ZnX’2 (wherein the symbol is as defined above) in the presence of one or more metals that are selected from among magnesium and magnesium alloys.

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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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A method for using amine-borane complexes directly in palladium catalyzed borylation has been developed. The reaction proceeds through the sequential formation of a boronium species followed by deprotonation leading to the aminoborane. This reagent is then directly used in the borylation process leading, after work-up, to various boronic acid derivatives. The reaction was applied to (hetero)aryl triflates, iodides, bromides and chlorides.

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Reference:
Benzothiophene – Wikipedia,
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A range of different N- and S-containing heterocyclic bromides can be efficiently coupled with gaseous ammonia in the presence of copper(II) acetylacetonate [Cu(acac)2] as catalyst and in the absence of additional ligands. Unstable aminothiophenes and aminobenzothiophenes can be further reacted in situ to afford functionalized derivatives. Copyright

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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem