6774-39-6

Upstream product

• 312612-67-2 1-(2-(methylthio)phenyl)-2-phenylacetylene 
• 6287-82-7 2,3-dibromobenzo[b]thiophene 
• 591-50-4 iodobenzene 
• 98437-23-1 benzo[b]thiophene-2-boronic acid 
• 33775-94-9 2-(methylthio)iodobenzene 
• 1207-95-0 2-phenylbenzo[b]thiophene 
• 95-15-8 Benzo[b]thiophene 
• 108-86-1 bromobenzene 
• 536-74-3 phenylacetylene 
• 7342-82-7 3-Bromothianaphthene 
• 462-06-6 fluorobenzene 

Downstream Products

• 178614-24-9 3-(4-(methylsulfonyl)phenyl)-2-phenylbenzo[b]thiophene 
• 1207-95-0 2-phenylbenzo[b]thiophene 
• 1337915-86-2 1-(2-phenylbenzo[b]thiophen-3-yl)perfluorocyclopentene 
• 1337915-85-1 3,3'-(perfluorocyclopent-1-ene-1,2-diyl)bis(2-phenylbenzo[b]thiophene) 
• 1337915-89-5 1-(1,1-dimethyl-2-phenylbenzo[b]silol-3-yl)-2-(2-phenylbenzo[b]thiophen-3-yl)perfluorocyclopentene 
• 78176-97-3 phenyl-2(hydroxy-1 cyclohexyl)-3 benzothiophene 

Relevant academic research and scientific papers

Oxone-mediated halocyclization/demethylation of 2-alkynylthioanisoles with sodium halides towards 3-halobenzo[b]thiophenes

An efficient and practical protocol for the Oxone-mediated halocyclization/demethylation of 2-alkynylthioanisoles towards valuable 3-halobenzo[b]thiophenes is described. Structurally diverse 3-halobenzothiophenes were obtained in good to excellent yields

Dephosphinylative [4 + 2] Benzannulation of Phosphinyl Ynamines: Application to the Modular Synthesis of Polycyclic Aromatic Amines

A series of 9-amino-10-halophenanthrenes were synthesized through a one-pot process, including dephosphinylative Sonogashira–Hagihara coupling of 2-bromobiphenyls with air-stable phosphinyl ynamines, followed by halonium-promoted [4 + 2] benzannulation of the resulting 2-(aminoethynyl)biphenyls. Nonsubstituted and methyl-substituted 2-bromobiphenyls rapidly underwent the Sonogashira–Hagihara aminoethynylation and the halogenative Friedel–Crafts benzannulation to provide the corresponding amino(halo)phenanthrenes in high yields, while electron-sufficient and -deficient substrates did slowly undergo the former and the latter to result in low yields, respectively. This protocol worked well for the syntheses of highly π-extended aminophenanthrenes and aminobenzonaphthothiophenes with different optical properties. Further application of this approach between 2,2″- and 2′,5′-dibromo-p-terphenyls with phosphinyl ynamines led to the regioselective formation of 6,13-diamino-5,12-dihalo- and 5,12-diamino-6,13-dihalo-dibenz[a,h]anthracenes via dual aminoethynylation and [4 + 2] benzannulation. The obtained analogues showed different ultraviolet–visible absorption and photoluminescence spectra with different emission quantum yields in CH2Cl2 solution and the powder state.

Toward a Greener Barluenga-Valdés Cross-Coupling: Microwave-Promoted C-C Bond Formation with a Pd/PEG/H2O Recyclable Catalytic System

A green Barluenga-Valdés cross-coupling reaction for the synthesis of 1,1-diarylethylenes using palladium catalysis has been developed. The new catalytic system based on Pd/Xphos-SO3Na or Pd/MeDavephos-CF3SO3 in PEG/H2O under microwave irradiation was found to be the best conditions for this transformation. The recyclability of the palladium catalyst system was also studied, and it was found to be active over nine runs without significant loss in its activity.

Sodium halides as the source of electrophilic halogens in green synthesis of 3-halo- and 3,n-dihalobenzo[b]thiophenes

A convenient methodology for the synthesis of mono- and di-halogenated benzo[b]thiophenes is described herein, which utilizes copper(II) sulfate pentahydrate and various sodium halides in the presence of substituted 2-alkynylthioanisoles. The proposed met

Rh-Catalyzed Dehydrogenative Cyclization Leading to Benzosilolothiophene Derivatives via Si-H/C-H Bond Cleavage

Straightforward syntheses leading to π-extended benzosilolothiophene (BST) derivatives by Rh-catalyzed dehydrogenative cyclization reactions have been developed. Electron-deficient ligands were effective for the reactions, and dppe-F20 gave the

In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides

A thorough investigation of the challenging Pd-catalyzed fluorination of five-membered heteroaryl bromides is presented. Crystallographic studies and density functional theory (DFT) calculations suggest that the challenging step of this transformation is

Environmentally benign process for the synthesis of 2,3-disubstituted benzo[b]thiophenes using electrophilic cyclization

We have developed a greener process for the synthesis of 2,3-disubstituted benzo[b]thiophenes using electrophilic cyclization as a key step. Our method not only employs an environmentally friendly solvent ethanol, but also utilizes safe and inexpensive in

Directed metalation and regioselective functionalization of 3-bromofuran and related heterocycles with NaHMDS

A mild and regioselective functionalization protocol for 3-bromofuran and analogs has been developed. Selective metalation and functionalization of C2 can be achieved as a result of the directing effect of the adjacent electron-withdrawing bromo group. In addition, the C5 position can also be selectively functionalized by blocking the C2 position via silylation or by simply controlling the reaction temperature. These functionalized compounds bearing a C3 bromo substituent may be further elaborated by utilizing a Suzuki-Miyaura cross-coupling procedure.

Halocyclization of 2-alkynylthioanisoles by cupric halides: synthesis of 2-substituted 3-halobenzo[b]thiophenes

Reaction of 2-alkynylthioanisoles 3 with 2 equiv of CuX2 (X=Br or Cl) in refluxing CH3CN for 2.5 h gave the 2-substituted 3-halobenzo[b]thiophenes 4 in good yields.

Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling anphilic cyclization of terminal acetylenes

2,3-Disubstituted benzo[b]thiophenes have been prepared in excellent yields via coupling of terminal acetylenes with commercially available o-iodothioanisole in the presence of a palladium catalyst and subsequent electrophilic cyclization of the resulting