220659-84-7

Upstream product

• 90-90-4 (4-bromophenyl)(phenyl)methanone 
• 1066-54-2 trimethylsilylacetylene 
• 28144-70-9 anthranilic acid amide 
• 16116-78-2 (4-bromophenyl)(trimethylsilyl)acetylene 
• 6136-66-9 4-iodobenzophenone 

Downstream Products

• 1378416-19-3 (2-(4-((trimethylsilyl)ethynyl)phenyl)ethene-1,1,2-triyl)tribenzene 
• 1503-49-7 p-cyanobenzophenone 
• 1620024-22-7 4-[(4-ethynyl-phenyl)-phenyl-methylene]-2,6-diphenyl-4H-pyran 
• 1620027-64-6 [Pt(4-[(4-ethynyl-phenyl)-phenyl-methylene]-2,6-diphenyl-4H-pyran-H)(P(Tol)3)2(C₂(C₄H₂S)CHO)] 
• 1620027-63-5 [Pt(4-[(4-ethynyl-phenyl)-phenyl-methylene]-2,6-diphenyl-4H-pyran-H)(P(Tol)3)2(C₂(C₄H₂O)CHO)] 

Relevant academic research and scientific papers

Aromatization as an Impetus to Harness Ketones for Metallaphotoredox-Catalyzed Benzoylation/Benzylation of (Hetero)arenes

Herein we report ketones as feedstock materials in radical cross-coupling reactions under Ni/photoredox dual catalysis. In this approach, simple condensation first converts ketones into prearomatic intermediates that then act as activated radical sources for cross-coupling with aryl halides. Our strategy enables the direct benzylation/benzoylation of (hetero)arenes under mild reaction conditions with high functional group tolerance.

Multi-fold Sonogashira coupling: A new and convenient approach to obtain tetraalkynyl anthracenes with tunable photophysical properties

For the first time, a direct single-step one-pot route to access nine new symmetric tetraalkynylated anthracenes via Pd(CH3CN)2Cl2/cataCXiumA catalyzed tetra-fold Sonogashira coupling is reported. Five of these tetraalkynylated anthracenes have been crystallographically characterized, with two of them exhibiting multiple interactions that significantly shorten the inter-planar distances in the solid-state structure. The rich photophysical properties exhibited by these molecules hold immense promise for future applications in sensors and optoelectronic devices. Two of the considered tetraalkynylated anthracenes comprising a D-π-A-π-D motif demonstrate solvatochromism and halochromism, with one of them showing a low bandgap of 1.79 eV. The remaining compounds demonstrate bandgaps in the range of 1.79-2.04 eV.

Diboron-Assisted Copper-Catalyzed Z-Selective Semihydrogenation of Alkynes Using Ethanol as a Hydrogen Donor

We herein describe a B2Pin2-assisted copper-catalyzed semihydrogenation of alkynes. A variety of alkenes were obtained in good to excellent yields with Z-selectivity under mild reaction conditions. Mechanistic studies indicated that a transfer hydrogenation process was involved and ethanol acted as both a solvent and a hydrogen donor in this reaction. The present protocol enabled convenient synthesis of deuterium-substituted Z-alkenes such as Z-Combretastain A4-d2 in a high deuteration ratio by using readily available ethanol-d1 as the deuterium source.

Aryl Nitriles from Alkynes Using tert -Butyl Nitrite: Metal-Free Approach to C≡C Bond Cleavage

Alkyne C≡C bond breaking, outside of alkyne metathesis, remains an underdeveloped area in reaction discovery. Recently, nitrogenation has been reported to allow nitrile formation from alkynes. A new protocol for the metal-free C≡C bond cleavage of terminal alkynes to produce nitriles is reported. This method provides an opportunity to synthesize a vast range of nitriles containing aryl, heteroaryl, and natural product derivatives (38 examples). In addition, the potential of tBuONO to act as a powerful nitrogenating agent for terminal aryl alkynes is demonstrated. (Figure Presented).

Conjugated polymer nanoparticles with aggregation induced emission characteristics for intracellular Fe3+ sensing

In this article, a novel zwitterionic conjugated polyelectrolyte containing tetraphenylethene unit was synthesized via Pd-catalyzed Sonogashira reaction. The resulting polymer (P2), which exhibited typical aggregation-induced emission (AIE) properties, wa

Palladium end-capped polyynes via oxidative addition of 1-haloalkynes to Pd(PPh3)4

Reported here is the use of 1-haloacetylenes and 1-halopolyynes as synthons for the preparation of new palladium(II) end-capped polyynes. The 1-haloalkynes were obtained in a series of transformations from para-substituted bromoarenes that included Sonogashira coupling followed by halogenation and chain elongation via Cadiot-Chodkiewicz protocol. The key step for the synthesis of metal complexes was oxidative addition of 1-haloalkynes to Pd(PPh3)4, which allowed obtaining a series of metal compounds 1-5-CnX with carbon chains up to hexatriyne in 75-100% yield. All the compounds were characterized by NMR and HRMS or elemental analysis. The 13C spectra of the 1-haloalkynes showed interesting, although expected, shifts of the carbon chain atoms close to the halogen termini. X-ray crystal structures were obtained for three polyynes-two butadiynes (2-C4[Pd]Br and 3-C4[Pd]Br) and one hexatriyne (1-C6[Pd]Br)-and the latter is the first reported X-ray crystal structure of palladium end-capped hexatriyne.

Fluorescence responsive conjugated poly(tetraphenylethene) and its morphological transition from micelle to vesicle

A crown ether-functionalized poly(tetraphenylethene) (AP-TPE) is synthesized and the rotation of the TPE group is successfully restricted via the complexation of crown ether and organic ammonium salts, leading to a stepwise enhanced fluorescence accompani

Aerobic oxynitration of alkynes with tBuONO and TEMPO

An efficient method for stereoselective nitroaminoxylation of alkyne has been reported. The reaction enjoys a broad substrate scope, good functional group tolerance, and high yields. Synthetically useful α-nitroketones can be accessed through these products in a single step.

Luminogenic materials constructed from tetraphenylethene building blocks: Synthesis, aggregation-induced emission, two-photon absorption, light refraction, and explosive detection

Luminogenic molecules [(TPE)3 (1), TPE-C = C-TPE-C = C-TPE (2), and TPE-C≡C-TPE-C≡C-TPE (3)] and their polymers P1-P3 are constructed from tetraphenylethene (TPE) building blocks in high yields by Suzuki, Witting, and Sonogashira coupling react

Metal-free oxidative trifluoromethylthiolation of terminal alkynes with CF3SiMe3 and elemental sulfur

A metal-free oxidative trifluoromethyl-thiolation of terminal alkynes using readily available CF3SiMe3 and elemental sulfur at room temperature has been developed. This reaction provides an efficient and convenient method for the preparation of alkynyl trifluoromethyl sulfides bearing a wide range of functional groups. Preliminary investigation revealed that elemental sulfur instead of air acted as the oxidant.