1296819-23-2

Upstream product

• 17763-67-6 Phenyl triflate 
• 1207-95-0 2-phenylbenzo[b]thiophene 
• 95-15-8 Benzo[b]thiophene 
• 583-53-9 2,3-dibromobenzene 
• 98437-23-1 benzo[b]thiophene-2-boronic acid 
• 583-55-1 1-Bromo-2-iodobenzene 
• 143888-85-1 (2-bromophenyl)methanethiol 
• 89-98-5 2-chloro-benzaldehyde 
• 5394-13-8 2-bromo-1-benzothiophene 
• 244205-40-1 (2-bromophenyl)boronic acid 
• 63724-94-7 2-deuteriobenzothiophene 

Downstream Products

• 1542124-28-6 C₁₈H₁₄OS 
• 1542125-52-9 C₁₆H₁₁BrOS 

Relevant academic research and scientific papers

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

Transition-Metal-Free Heterobiaryl Synthesis via Aryne Coupling

We disclose, for the first time, an efficient route for the construction of various heterobiaryl backbones in fair to excellent yields using the Aryne coupling methodology. This study outlined the remarkable effect of external chelating ligands and salt additives on the heterocyclic partner reactivity in the aryne coupling reaction.

Bay-Substituted Thiaza[5]helicenes: Synthesis and Implications on Structural and Spectroscopic Properties

A series of bay-substituted thiaza[5]helicenes was synthesized to investigate the effect of different substituents on the properties of these helicenes. These thiaza[5]helicenes with different substituents were prepared in a straightforward manner through indole- and benzo[b]thiophene synthesis, palladium-catalyzed Suzuki coupling, oxidative cyclization, and functional group interconversion reactions. We investigated the impact of these different bay area substituents compared to the unsubstituted thiaza[5]helicene on the structural parameters and studied the steady-state electronic spectroscopy of these thiaza[5]helicenes in toluene and acetonitrile. We found that different functional groups influence the solid state structure and spectroscopic properties, but a single substituent in the bay area of a thiaza[5]helicene was not enough to prevent enantiomerization at room temperature.

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.

Regioselective Direct C2 Arylation of Indole, Benzothiophene and Benzofuran: Utilization of Reusable Pd NPs and NHC-Pd@MNPs Catalyst for C–H Activation Reaction

Abstract: A regioselective C2 arylation of indoles, benzothiophene and benzofuran without directing group has been accomplished using economically cheap Pd NPs and NHC-Pd@MNPs catalyst. The reusable catalyst is efficiently employed to access C2 arylated heterocycles in good to excellent yield. The reusability of the catalyst is studied up to five cycles and a gram-scale synthesis has been achieved. The reaction mechanism is well supported by control experiments and literature precedents. Grapic Abstract: [Figure not available: see fulltext.]

Electrochemical Synthesis of Thienoacene Derivatives: Transition-Metal-Free Dehydrogenative C?S Coupling Promoted by a Halogen Mediator

The first electrochemical dehydrogenative C?S bond formation leading to thienoacene derivatives is described. Several thienoacene derivatives were synthesized by dehydrogenative C?H/S?H coupling. The addition of nBu4NBr, which catalytically promoted the reaction as a halogen mediator, was essential.

Ag(I)-C-H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[ b]thiophenes

The first example of near-room-temperature α-arylation of benzo[b]thiophenes is reported. The discovery rests on the observation of a switch in α-/β-regioselectivity at different loadings of Pd2(dba)3·CHCl3 in the coupling between benzo[b]thiophene and 4-iodotoluene. We show that this unprecedented regioselectivity switch is driven by a Ag(I)-mediated C-H activation at the α-C-H position, which becomes the dominant mode of reactivity at low concentrations of Pd. Competition experiments, kinetic studies, KIE, and D/H scrambling experiments have been carried out supporting this mechanism.

SPIRO COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE COMPRISING SAME

The present specification relates to a spiro structure compound and an organic light emitting device including the same.

General method for functionalized polyaryl synthesis via aryne intermediates

A method for base-promoted arylation of arenes and heterocycles by aryl halides and aryl triflates is described. Additionally, in situ electrophilic trapping of ArLi intermediates generated in the reaction of benzyne with deprotonated arenes or heterocycles has been developed, providing rapid and easy access to a wide range of highly functionalized polyaryls. Base-promoted arylation methodology complements transition-metal-catalyzed direct arylation and allows access to structures that are not easily accessible via other direct arylation methods. The reactions are highly functional-group tolerant, with alkene, ether, dimethylamino, trifluoromethyl, ester, cyano, halide, hydroxyl, and silyl functionalities compatible with reaction conditions.

Synthesis of functionalized polycyclic aromatic compounds via a formal [2 + 2]-cycloaddition

A base-promoted formal [2 + 2]-cycloaddition of 2-acyl-2′-vinyl-1, 1′-biaryls was developed to provide polycyclic cyclobutanols as a step toward the synthesis of substituted polycyclic aromatic hydrocarbons and their heterocyclic analogues.