20608-83-7

Upstream product

• 872-31-1 3-Bromothiophene 
• 583-53-9 2,3-dibromobenzene 
• 188290-36-0 thiophene 
• 615-36-1 2-bromoaniline 
• 583-55-1 1-Bromo-2-iodobenzene 
• 214360-70-0 4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane 
• 6165-69-1 Thien-3-ylboronic acid 
• 129112-25-0 2-(trifluoromethanesulfonyl)oxy-bromobenzene 

Downstream Products

• 1234675-30-9 N-(8H-indeno[2,1-b]thiophen-8-ylidene)-2,6-diisopropylaniline 
• 1404452-46-5 5-(2-(thiophen-3-yl)phenyl)pent-4-yn-1-ol 
• 1404452-06-7 3-(2-(5-bromopent-1-ynyl)phenyl)thiophene 
• 1332483-68-7 isopropyl[2-(thiophene-3-yl)phenyl]phosphine oxide 
• 1252259-79-2 2-(2-dimethylsilylphenyl)-3-thiophen 

Relevant academic research and scientific papers

Redox-Divergent Construction of (Dihydro)thiophenes with DMSO

Thiophene-based rings are one of the most widely used building blocks for the synthesis of sulfur-containing molecules. Inspired by the redox diversity of these features in nature, we demonstrate herein a redox-divergent construction of dihydrothiophenes, thiophenes, and bromothiophenes from the respective readily available allylic alcohols, dimethyl sulfoxide (DMSO), and HBr. The redox-divergent selectivity could be manipulated mainly by controlling the dosage of DMSO and HBr. Mechanistic studies suggest that DMSO simultaneously acts as an oxidant and a sulfur donor. The synthetic potentials of the products as platform molecules were also demonstrated by various derivatizations, including the preparation of bioactive and functional molecules.

NOVEL ORGANIC COMPOUND AND MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME AND ORGANIC ELECTROLUMINESCENT DEVICES COMPRISING THE SAME

The present invention provides a novel organic compound represented by chemical formula 1, a material for an organic electroluminescent device including the organic compound, and an organic electroluminescent device. The present invention can improve thermal stability, color purity, and device life.

Transition-Metal-Free Approach for the Direct Arylation of Thiophene: Experimental and Theoretical Investigations towards the (Het)-Aryne Route

This paper presents the results of our investigations on the arylation of thiophene using the transition-metal-free “aryne coupling” methodology. The reaction was studied by both experiment and computation (density functional theory) and comparison with phenyllithium was established. In parallel, the effects of the ligand and the salt on the coupling reaction were examined. The results underline the remarkable effect of such additives on the coupling reaction and the potency of the method to construct hetaryl–aryl backbones which open up promising access to a wide range of heterobiaryl structures using the novel “Het-Aryne” route.

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.

Rhodium-catalyzed intramolecular C-H silylation by silacyclobutanes

Silacyclobutane was discovered to be an efficient C-H bond silylation reagent. Under the catalysis of RhI/TMS-segphos, silacyclobutane undergoes sequential C-Si/C-H bond activations, affording a series of π-conjugated siloles in high yields and regioselectivities. The catalytic cycle was proposed to involve a rarely documented endocyclic β-hydride elimination of five-membered metallacycles, which after reductive elimination gave rise to a Si-RhI species that is capable of C-H activation. Old reagent, new reactivity: Silacyclobutane was discovered to be an efficient C-H bond silylation reagent under the catalysis of Rh/TMS-segophos. This new reactivity was attributed to a key Si-RhI intermediate formed through a Si-C activation, endocyclic β-H elimination and reductive elimination cascade. A wide array of siloles was obtained in high yields and excellent regioselectivities.

AgONO-Assisted Direct C-H Arylation of Heteroarenes with Anilines

A novel copper-catalyzed C-H arylation of heteroarenes with anilines by an in situ diazonium reaction is established by using silver nitrite (AgONO) as an unconventional nitrosating reagent under acid-free conditions. It provides a complementary approach for the C-H arylation of electron-rich heteroarenes with aromatic amines affording a variety of heterobiaryls in moderate to good yields.

Expeditious synthesis of tetrasubstituted helical alkenes by a cascade of palladium-catalyzed C-H activations

Twisted molecules: A modular approach for the synthesis of tetrasubstituted helical alkenes by a palladium-catalyzed norbornene-mediated domino reaction is presented. This intermolecular domino process allows the formation of three C-C bonds in one operation through a C-H activation/carbopalladation/C-H activation sequence. Copyright

Palladium-catalyzed cyclocoupling of 2-halobiaryls with isocyanides via the cleavage of carbon-hydrogen bonds

(Figure Presented) To demonstrate the utility of isocyanides in catalytic C-H bond functionalization reactions, a palladium-catalyzed cyclocoupling reaction of 2-halobiaryls with isocyanides was developed. The reaction afforded an array of fluorenone imine derivatives via the cleavage of a C-H bond at the 2′-position of 2-halobiaryls. The use of 2,6-disubstituted phenyl isocyanide was crucial for this catalytic cyclocoupling reaction to proceed. The reaction was applicable to heterocyclic and vinylic substrates, allowing the construction of a wide range of ring system. The large kinetic isotope effect observed (kH/kD = 5.3) indicates that C-H bond activation was the turnover-limiting step in this catalysis.

An efficient synthesis of novel spiro[[8H]indeno[2,1-b]-thiophene-8,9′-fluorene] building block for blue light-emitting materials

We have developed efficient synthetic routes to obtain a novel building block spiro[[8H]indeno[2,1-b]thiophene-8,9′-fluorene] (SITF), a monothiophene-containing spirobifluorene analogue, and constructed blue light-emitting materials, including 2′,7′-bis([

Synthesis of fluoren-9-ones by the palladium-catalyzed cyclocarbonylation of o-halobiaryls

The synthesis of various substituted fluoren-9-ones has been accomplished by the palladium-catalyzed cyclocarbonylation of o-halobiaryls. The cyclocarbonylation of 4′-substituted 2-iodobiphenyls produces very high yields of 2-substituted fluoren-9-ones bearing either electron-donating or electron-withdrawing substituents. 3′-Substituted 2-iodobiphenyls afford 3-substituted fluoren-9-ones in excellent yields with good regioselectivity. This chemistry has been successfully extended to polycyclic fluorenones and fluorenones containing fused isoquinoline, indole, pyrrole, thiophene, benzothiophene, and benzofuran rings.