4805-17-8

Usage

Uses

Used in Organic Material Synthesis:
2-(phenylethynyl)thiophene is used as a building block for synthesizing various organic materials, such as conducting polymers and organic semiconductors, due to its unique structure and properties that contribute to the performance of these materials.
Used in Organic Electronics:
In the field of organic electronics, 2-(phenylethynyl)thiophene is utilized as a component in the development of devices like organic light-emitting diodes (OLEDs) and organic photovoltaic cells, capitalizing on its good electron transport properties.
Used in Medical Imaging:
2-(phenylethynyl)thiophene is studied for its potential use in medical imaging applications, leveraging its fluorescent properties and bioconjugation capabilities to enhance imaging techniques and diagnostics.

Upstream product

• 91228-44-3 2-thienylphenyliodonium tosylate 
• 536-74-3 phenylacetylene 
• 4298-52-6 2-ethynyl-thiophene 
• 591-50-4 iodobenzene 
• 1003-09-4 2-bromothiophene 
• 3757-88-8 tributylstannylethynylbenzene 
• 932-88-7 1-iodo-2-phenylethyne 
• 54663-78-4 tributyl(thien-2-yl)stannane 
• 3437-95-4 2-Iodothiophene 
• 764-93-2 1-decyne 
• 1719-19-3 2-Methyl-4-phenyl-3-butyn-2-ol 
• 133844-84-5 2-methyl-4-(thien-2-yl)but-3-yn-2-ol 
• 53034-24-5 2-thienyllead(IV) triacetate 
• 188290-36-0 thiophene 

Downstream Products

• 30135-07-0 1-phenyl-2-(2-thienyl)ethanedione 
• 18853-37-7 5,6-diphenyl-4H-cyclopenta--thiophen-4-one 
• 18853-36-6 2-phenyl 3-(2-thienyl)-<1H>-inden-1-one 
• 131269-20-0 2-(2'-thienyl)3-phenyl-<1H>-inden-1-one 
• 131269-31-3 2,3-bis(thiophen-2-yl)-1H-inden-1-one 
• 131269-30-2 C₁₇H₁₀OS₂ 
• 56365-78-7 5-Phenyl-6-thiophen-2-yl-cyclopenta[b]thiophen-4-one 
• 3783-65-1 (Z)-2-(β-styryl)thiophene 
• 3783-65-1 (E)-2-(2-phenylethenyl)thiophene 
• 1430206-26-0 C₁₉H₁₅NOS₂ 
• 115257-02-8 5,5'-bis(phenylethynyl)-2,2'-dithiophene 
• 833-50-1 2-phenylbenzo[d]oxazole 
• 23999-63-5 2-thiophen-2-yl-benzooxazole 

Relevant academic research and scientific papers

Zeolitic imidazolate frameworks-67 (ZIF-67) supported PdCu nanoparticles for enhanced catalytic activity in Sonogashira-Hagihara and nitro group reduction under mild conditions

A bimetallic PdCu supported on amine functionalized ZIF-67 is shown to be efficient catalyst in Sonogashira-Hagihara coupling reaction of aryl iodides at room temperature and aryl bromides at 40 oC. In addition, the catalyst is used in the reduction of 4-

Simple and efficient diaryl alkyne synthesis method

The embodiment of the invention discloses a simple and efficient diaryl alkyne synthesis method. The method comprises the steps of by taking arylmethylbenzotriazole and aromatic aldehyde as raw materials, carrying out addition and double-beta-elimination reaction under the action of bis (trimethylsilyl) amino salt MN (SiMe3) 2 to synthesize diaryl alkyne by a one-pot method. The raw materials and chemical reagents used in the method are easy to obtain, the reaction conditions are mild, the operation is simple, the substrate universality is good, the product yield is high, and the method is a simple and efficient diaryl alkyne synthesis method.

A Waste-Minimized Approach to Cassar-Heck Reaction Based on POLITAG-Pd0 Heterogeneous Catalyst and Recoverable Acetonitrile Azeotrope

Three different Pd0-based heterogeneous catalysts were developed and tested in the Cassar–Heck reaction (i. e., copper-free Sonogashira reaction) aiming at the definition of a waste minimized protocol. The cross-linked polymeric supports used in this investigation were designed to be adequate for different reaction media and were decorated with different pincer-type ionic ligands having the role of stabilizing the formation and dimension of palladium nanoparticles. Among the ionic tags tested, bis-imidazolium showed the best performances in terms of efficiency and durability of the metal catalytic system. Eventually, aqueous acetonitrile azeotrope was selected as the reaction medium as it allowed the best catalytic efficiency combined with easy recovery and reuse. Finally, the synergy between the selected catalyst and reaction medium allowed to obtain highly satisfactory isolated yields of a variety of substrates while using a low amount of metal catalyst. The high performance of the designed POLymeric Ionic TAG (POLITAG)-Pd0, along with its good selectivity achieved in a copper-free process, also led to a simplified purification procedure allowing the minimization of the waste generated as also proven by the very low E-factor values (1.4–5) associated.

Highly efficient synthesis of 1,2-disubstituted acetylenes derivatives from the cross-coupling reactions of 1-bromoalkynes with organotitanium reagents

A Highly efficient route for the synthesis of 1,2-disubstituted acetylene derivatives has been developed by nickel catalyzed cross-couplings of alkynyl halides with aryl titanium reagents under mild conditions. This has given corresponding cross-coupling products good to excellent isolated yields of up to 92 %. The aryls bearing electron-donating or electron-withdrawing groups in either alkynylhalides or aryltitanium substrates gave cross-coupling products good yields. This process was simple and easily performed, which provides an efficient method for the synthesis of 1,2-disubstituted acetylenes derivatives.

Highly Efficient Synthesis of 2-Substituted Benzo[ b ]furan Derivatives from the Cross-Coupling Reactions of 2-Halobenzo[ b ]furans with Organoalane Reagents

A highly efficient and simple route for the synthesis of 2-substituted benzo[ b ]furans has been developed by palladium-catalyzed cross-coupling reaction of 2-halobenzo[ b ]furans with aryl, alkynyl, and alkylaluminum reagents. Various 2-aryl-, 2-alkynyl-, and 2-alkyl-substituted benzo[ b ]furan derivatives can be obtained in 23-97% isolated yields using 2-3 mol% PdCl 2/4-6 mol% XantPhos as the catalyst under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in 2-halobenzo[ b ]furans gave products in 40-97% isolated yields. In addition, aluminum reagents containing thienyl, furanyl, trimethylsilanyl, and benzyl groups worked efficiently with 2-halobenzo[ b ]furans as well, and three bioactive molecules with 2-substituted benzo[ b ]furan skeleton were synthesized. Furthermore, the broad substrates scope and the typical maintenance of vigorous efficiency on gram scale make this protocol a potentially practical method to synthesize 2-substituted benzo[ b ]furan derivatives. On the basis of the experimental results, a possible catalytic cycle has been proposed.

Decarbonylative Sonogashira Cross-Coupling of Carboxylic Acids

Decarbonylative Sonogashira cross-coupling of carboxylic acids by palladium catalysis is presented. The carboxylic acid is activated in situ by the formation of a mixed anhydride and further decarbonylates using the Pd(OAc)2/Xantphos system to provide an aryl-Pd intermediate, which is intercepted by alkynes to access the traditional Pd(0)/(II) cycle using carboxylic acids as ubiquitous and orthogonal electrophilic cross-coupling partners. The methodology efficiently constructs new C(sp2)-C(sp) bonds and can be applied to the derivatization of pharmaceuticals. Mechanistic studies give support to decarbonylation preceding transmetalation in this process.

Ligand-Promoted Alkynylation of Aryl Ketones: A Practical Tool for Structural Diversity in Drugs and Natural Products

Conversion of the numerous aryl ketones into aryl electrophiles via Ar-C(O) cleavage remains a challenging yet highly desirable transformation in Sonogashira-type coupling. Herein, we report a palladium-catalyzed ligand-promoted alkynylation of unstrained aryl ketones. The protocol allows the alkynylation to be carried out in a one-pot procedure with broad functional-group tolerance and substrate scope. The potential applications of this protocol in drug discovery and chemical biology are further demonstrated by late-stage diversification of a number of pharmaceuticals and natural products. More importantly, two different biologically important fragments derived from a pharmaceutical and natural product could be connected by the consecutive alkynylation of ketones. Distinct from aryl halides in conventional Sonogashira reactions, the protocol provides a practical tool for the 1,2-bifunctionalization of aryl ketone by merging ketone-directed ortho-C-H activation with ligand-promoted ipso-Ar-C(O) alkynylation.

Xantphos-coordinated palladium dithiolates: Highly efficient catalyst for decarboxylative Sonogashira reaction into corresponding alkynes

This work reports Xantphos-coordinated palladium dithiolate complexes as catalysts for decarboxylative Sonogashira coupling reaction of phenyl propiolic acid and 2-butynoic acid with various iodoarenes. These palladium aryl dithiolate complexes were synthesized and characterized by 1H and 31P nuclear magnetic resonance (NMR) spectroscopy, melting point, and elemental analysis (CHNS). Synthetic utility for the reported protocol is explored for the effect of various functional groups on the yield of corresponding heteroaryl alkynes. The current protocol showed excellent catalytic activity towards decarboxylative alkynylation reaction with high turn-over number (TON) up to 105 and turn-over frequency (TOF) up to 104 h?1. The catalyst could be recycled up to six recycles without losing its catalytic activity. The in situ generation of palladium nanoparticles (PdNPs) was observed after the third recycle, and the amount was significant after the sixth recycle, which were confirmed and characterized by powder X-ray diffraction (XRD), scanning electron microscope (SEM), and energy-dispersive X-ray (EDX) analysis and high-resolution transmission electron microscopy (HR-TEM). The catalytic activity of the reaction is attributed to the formation of PdNPs.

Facile one-pot synthesis of diarylacetylenes from arylaldehydes: Via an addition-double elimination process

A practical one-pot protocol has been developed to synthesize diarylacetylenes from arylaldehydes by treatment with 1-(arylmethyl)benzotriazoles and LiN(SiMe3)2. The reaction proceeded through imine formation, Mannich-type addition and double elimination to deliver products in up to 99% yields with broad substrate scope. In addition, gram-scale synthesis of 1-bromo-4-(phenylethynyl)benzene has been demonstrated.

Selective Phosphoranation of Unactivated Alkynes with Phosphonium Cation to Achieve Isoquinoline Synthesis

We herein develop a selective phosphoranation of alkynes with phosphonium cation, which directs a concise approach to isoquinolines from unactivated alkyne and nitrile feedstocks in a single step. Mechanistic studies suggest that the annulation reaction is initiated by the unprecedented phosphoranation of alkynes, thus representing a unique reaction pattern of phosphonium salts and distinguishing it from existing protocols that largely rely on the utilization of highly functionalized imines/oximes and/or highly polarized alkynes.