1849-28-1

Upstream product

• 3757-88-8 tributylstannylethynylbenzene 
• 88016-29-9 μ-oxobis[(trifluoromethanesulfonato)(phenyl)iodine] 
• 624-38-4 para-diiodobenzene 
• 536-74-3 phenylacetylene 
• 3112-88-7 Benzyl phenyl sulfone 
• 15164-44-0 p-(iodophenyl)carboxaldehyde 
• 5122-99-6 4-iodophenylboronic acid 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 1190376-20-5 4,4,5,5-tetramethyl-2-[4-(2-phenylethynyl)phenyl]-1,3,2-dioxaborolane 
• 637-87-6 1-Chloro-4-iodobenzene 
• 4706-43-8 1-benzyl-1H-benzotriazole 
• 100-44-7 benzyl chloride 
• 100-52-7 benzaldehyde 
• 25438-37-3 phenyl(trimethylsiloxy)acetonitrile 

Downstream Products

• 910537-34-7 triisopropyl-{4-[4-(4-phenylethynyl-phenylethynyl)-phenylethynyl]-phenylethynyl}-silane 
• 97765-42-9 1,4-bis(4-(phenylethynyl)phenylethynyl)benzene 
• 1170659-63-8 5-(4-methoxyphenyl)-2-{4-(phenylethynyl)phenyl}oxazole 
• 1170659-62-7 5-(3,4-dimethoxyphenyl)-2-{4-(phenylethynyl)phenyl}oxazole 
• 1170659-64-9 5-(naphthylen-2-yl)-2-{4-(phenylethynyl)phenyl}oxazole 
• 1168153-33-0 C₂₉H₁₉BrO₂S 
• 1198351-31-3 1-methyl-2-(4-(phenylethynyl)phenyl)-1H-pyrrole 
• 39859-81-9 1-(4-iodophenyl)-2-phenylethane-1,2-dione 
• 92866-00-7 4-ethynyltolane 
• 147492-76-0 1-(phenylethynyl)-4-[(trimethylsilyl)ethynyl]benzene 
• 13041-71-9 (E)-1-(4-iodophenyl)-2-phenylethene 
• 201480-89-9 2-(4-iodophenyl)-3-phenylquinoxaline 
• 106785-01-7 4,4'-bis(phenylethynyl)diphenylethyne 

Relevant academic research and scientific papers

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.

A new approach to large scale production of dimethyl sulfone: A promising and strong recyclable solvent for ligand-free Cu-catalyzed C-C cross-coupling reactions

Dimethyl sulfone (DMSN) was easily prepared through efficient oxidation of dimethyl sulfoxide (DMSO) and used as a strong and green solvent for organic reactions. A mixture of HNO3/NaOCl was used as an oxidizing agent for efficient oxidation of DMSO to DMSN. The effect of DMSN was evaluated for copper-catalyzed coupling reactions. It is worth noting that DMSN could play the role of a ligand for copper ions. A general survey was accomplished for various types of C-C cross-coupling reactions catalyzed by CuI in DMSN in the absence of any ligand. Moderate to good yields were achieved for Sonogashira, Heck, and Suzuki cross-coupling reactions. Finally, DMSN was recovered and reused for several consecutive runs without any loss of its activity.

The Direct Conversion of α-Hydroxyketones to Alkynes

Alkynes are highly important functional groups in organic chemistry, both as part of target structures and as versatile synthetic intermediates. In this study, a protocol for the direct conversion of α-hydroxyketones to alkynes is reported. In combination with the variety of synthetic methods that generate the required starting materials by forming the central C-C bond, it enables a highly versatile fragment coupling approach toward alkynes. A broad scope for this novel transformation is shown alongside mechanistic insights. Furthermore, the utility of our protocol is demonstrated through its application in concert with varied α-hydroxyketone syntheses, giving access to a broad spectrum of alkynes.

Supramolecular photocatalyst of Palladium (II) Encapsulated within Dendrimer on TiO2 nanoparticles for Photo-induced Suzuki-Miyaura and Sonogashira Cross-Coupling reactions

In this study, synthesis, characterization and catalytic performance of a novel supramolecular photocatalytic system including palladium (II) encapsulated within amine-terminated poly (triazine-triamine) dendrimer modified TiO2 nanoparticles (Pd (II) [PTATAD] @ TiO2) is presented. The obtained nanodendritic catalyst was characterized by FT-IR, ICP-AES, XPS, EDS, TEM, TGA and UV-DRS. The as-prepared nanodendritic catalyst was shown to be highly active, selective, and recyclable for the Suzuki–Miyaura and Sonogashira cross-coupling of a wide range of aryl halides including electron-rich and electron-poor and even aryl chlorides, affording the corresponding biaryl compounds in good to excellent yields under visible light irradiation. This study shows that visible light irradiation can drive the cross-coupling reactions on the Pd (II) [PTATAD] @ TiO2 under mild reaction conditions (27–30?°C) and no additional additives such as cocatalysts or phosphine ligands. So, we propose that the improved photoactivity predominantly benefits from the synergistic effects of Pd (II) amine-terminated poly (triazine-triamine) dendrimer on TiO2 nanoparticles that cause efficient separation and photogenerated electron–hole pairs and photoredox capability of nanocatalyst which all of these advantages due to the tuning of band gap of catalyst in the visible light region.

Conjugated mesoporous polyazobenzene–Pd(II) composite: A potential catalyst for visible-light-induced Sonogashira coupling

We herein report the direct harnessing of visible light energy by a novel semiconducting azobenzene-based colloidal porous organic polymer, B3-Azo4 amenable to post-synthetic Pd(II)-complexation for photo-induced Sonogashira coupling using polymer → metal energy transfer process. Completely mesoporous nano-sized particles of the obtained organic network manifested excellent Pd(II) coordinating ability and afforded desired catalytic products at room temperature under aerobic condition in aqueous medium. The protocol remained valid for different aromatic and aliphatic substrates as well. A possible reaction mechanism for photo-mediated Sonogashira coupling catalyzed by Pd-B3-Azo4 is also proposed.

Radiosynthesis of SPECT tracers: Via a copper mediated 123I iodination of (hetero)aryl boron reagents

A general method for the copper mediated nucleophilic 123I-iodination of (hetero)aryl boronic esters and acids has been developed. The broad substrate scope of this radiosynthetic approach allows access to [123I]DPA-713, [123I]IMPY, [123I]MIBG and [123I]IPEB that are four commonly used SPECT radiotracers. Our results infer that aryl boronic reagents can now be employed as common precursors for both fluorine-18 and iodine-123 radiolabelling.

Boronate ester post-functionalization of PPEs: versatile building blocks for poly(2,2′-(1-(4-(1,2-di(thiophen-2-yl)vinyl)phenyl)-2-(2,5-dioctylphenyl)ethene-1,2-diyl)dithiophene) and application in field effect transistors

A convenient and scalable strategy for post-functionalization of poly(phenylene-ethynylene)s and phenylene-ethynylene arrays from boronate ester derivatives using the thienyl group as an example. Furthermore, poly(2,2′-(1-(4-(1,2-di(thiophen-2-yl)vinyl)phenyl)-2-(2,5-dioctylphenyl)ethene-1,2-diyl)dithiophene) showed good field-effect transistor performance with an excellent mobility up to 0.723 cm2 V-1 s-1 and an on-off ratio of 104.

Copper(i) catalyzed Sonogashira reactions promoted by monobenzyl nicotinium chloride, a N-donor quaternary ammonium salt

A novel and effective catalytic system using monobenzylnicotinium chloride combined with copper(i) chloride was employed for the first time in Sonogashira cross-coupling reactions of phenylacetylene with various aryl halides. The goal was to use an efficient green media by using copper instead of palladium in metal-catalyzed coupling reactions. Monobenzyl nicotinium chloride, a quaternary ammonium salt containing a coordinating centre, plays an important role in this catalytic system and increases the efficiency of Cu(i) species during the reaction. A number of internal alkynes were produced in moderate to excellent yields in short reaction times in DMF at 135-140 °C. The efficiency of this catalytic system was compared with the copper-based catalyst obtained from dibenzylnicotinium chloride which has no N-donor active site, wherein lower activity was observed due to lack of a coordination site.

Position of substitution: A facile way to tune the spectroscopic properties of dimethylamino-substituted arylene-ethynylenes

A series of dimethylamino-substituted arylene-ethynylenes were synthesised by Sonogashira coupling reactions and characterised by the methods of 1H, 13C NMR, UV-Vis, fluorescence, HRMS and theoretical calculations. Effects on spectroscopic properties caus

Melamine-based microporous network polymer supported palladium nanoparticles: A stable and efficient catalyst for the sonogashira coupling reaction in water

A template consisting of a melamine-based microporous polymer network was synthesized and utilized as a solid support to stabilize palladium nanoparticles; the resulting Pd/SNW1 material showed good catalytic activity in copper-free Sonogashira coupling in water. Various aryl iodides were efficiently coupled with arylacetylenes under very low catalyst loadings in an environmentally benign medium. Hot filtration tests confirmed the heterogeneity of the catalyst, which was reused under the optimized conditions without any significant change in its activity. This simple preparation of the catalyst, the stability of the catalyst, product selectivity, and easy recovery and regeneration indicate the possible utilization of this catalytic system in a multitude of catalyzed reactions and industrial processes. Networking possibilities: A template consisting of melamine-based microporous polymer network is synthesized and utilized as a solid support to stabilize palladium nanoparticles; the resulting Pd/SNW1 material shows good catalytic activity in copper-free Sonogashira coupling in water. Various aryl iodides are efficiently coupled with arylacetylenes under very low catalyst loadings in an environmentally benign medium.