29778-29-8

Upstream product

• 591-18-4 1-Bromo-3-iodobenzene 
• 159015-72-2 dimethyl(2-phenylethynyl)silanol 
• 108-36-1 1,3-dibromobenzene 
• 536-74-3 phenylacetylene 
• 56280-66-1 diethyl(phenyl)aluminium 
• 100-58-3 phenylmagnesium bromide 
• 3132-99-8 m-bromobenzoic aldehyde 
• 4706-43-8 1-benzyl-1H-benzotriazole 
• 100-44-7 benzyl chloride 
• 6738-06-3 phenylethynylmagnesium bromide 
• 66107-31-1 3-bromophenyl trifluoromethanesulfonate 
• 13146-23-1 copper(I) phenylacetylenide 

Downstream Products

• 136459-74-0 1-phenyl-2-acetylene 
• 1151549-78-8 4-[2-[3-(2-phenylethynyl)phenyl]ethynyl]benzonitrile 
• 147492-78-2 1-ethynyl-3-(phenylethynyl)benzene 
• 1286734-48-2 4-(3-(phenylethynyl)phenyl)-2-methyl-3-butyn-2-ol 
• 111731-38-5 1-phenyl-2-(m-hydroxyphenyl)acetylene 
• 51624-44-3 1-(3-aminophenyl)-2-phenylacetylene 
• 19466-32-1 (Z)-1-bromo-3-styrylbenzene 
• 14064-45-0 (E)-3-bromostilbene 
• 40396-54-1 1-(3-bromophenyl)-2-phenylethane-1,2-dione 

Relevant academic research and scientific papers

FUNCTIONALIZED POLYCYCLIC AROMATIC HYDROCARBON COMPOUND AND LIGHT-EMITTING DEVICE INCLUDING THE SAME

Provided are a functionalized polycyclic aromatic hydrocarbon compound and a light-emitting device including the same. The functionalized polycyclic aromatic hydrocarbon compound is structurally stable, and exhibits high light-emission characteristics sin

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.

Sustainable Ligand-Free Heterogeneous Palladium-Catalyzed Sonogashira Cross-Coupling Reaction in Deep Eutectic Solvents

The commercially available and cheap Pd/C was found to promote Sonogashira couplings in the environmentally friendly choline chloride/glycerol eutectic mixture in the absence of external ligands. Under heterogeneous conditions, (hetero)aryl iodides were successfully coupled with both aromatic and aliphatic alkynes in yields ranging from 50 to 99 % within 3 h at 60 °C. The aforementioned catalytic system proved to be effective also towards electron-rich iodides, which are notoriously known to be poorly reactive in Pd-catalyzed Sonogashira coupling reactions. The eutectic mixture and the catalyst could easily and successfully be recycled up to four times with an E-factor as low as 24.4.

Design, synthesis and evaluation of 2-amino-imidazol-4-one derivatives as potent β-site amyloid precursor protein cleaving enzyme 1 (BACE-1) inhibitors

Inhibition of β-site amyloid precursor protein cleaving enzyme 1 (BACE1) to prevent brain β-amyloid (Aβ) peptide's formation is a potential effective approach to treat Alzheimer's disease. In this report we described a structure-based optimization of a series of BACE1 inhibitors derived from an iminopyrimidinone scaffold W-41 (IC50 = 7.1 μM) by Wyeth, which had good selectivity and brain permeability but low activity. The results showed that occupying the S3 cavity of BACE1 enzyme could be an effective strategy to increase the biological activity, and five compounds exhibited stronger inhibitory activity and higher liposolubility than W-41, with L-5 was the most potent inhibitor against BACE1 (IC50 = 0.12 μM, logP = 2.49).

Arylation of Terminal Alkynes by Aryl Iodides Catalyzed by a Parts-per-Million Loading of Palladium Acetate

Arylation of terminal alkynes (16 varieties) by aryl iodides (28 varieties) was achieved with a mol ppm loading level of palladium catalyst, where a variety of functional groups including heteroarenes were tolerated. Thus, the arylations were carried out in the presence of palladium acetate at ppm loadings and potassium carbonate in ethanol at 80 °C to give the corresponding internal alkynes in good to excellent yields. Synthesis of 2-phenyl-3-(phenylalkynyl)benzofuran was achieved by iterative use of the alkyne arylation under mol ppm catalytic conditions. Reaction-rate analysis, transmission electron microscopic (TEM) examination of the reaction mixture, and mercury-amalgamation test were performed to gain insight into the active species of the highly active ppm catalytic species. TEM examination of the reaction mixture revealed that palladium nanoparticles were generated in situ under the reaction conditions, and their cluster size was variable during the catalytic reaction. A variation in size of palladium particles suggested that the composition-decomposition process of Pd aggregates should take place in situ via monomeric palladium(0) species and/or fine palladium(0) clusters, which might be real catalytic species in this reaction.

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

A Highly efficient route for the synthesis of 1,2-disubstituted acetylene derivatives has been developed by palladium catalyzed cross-couplings of alkynyl halides with (hetero)aryl aluminium reagents under mild conditions. This has given corresponding cross-coupling products good to excellent isolated yields of up to 99%. The aryls bearing electron-donating or electron-withdrawing groups in either alkynylhalides or arylaluminum 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. On the basis of the experimental results, a possible catalytic cycle has been proposed.

A Sustainable, User-Friendly Protocol for the Pd-Free Sonogashira Coupling Reaction

We herein present a new catalytic system for the palladium-free Sonogashira coupling reaction. The catalytically active moiety is formed in situ, in a straightforward and user-friendly manner, by combining a widely available low-cost copper salt and an N-

Achiral Pyridine Ligand-Enabled Enantioselective Radical Oxytrifluoromethylation of Alkenes with Alcohols

A conceptually novel strategy with achiral pyridine as the ancillary ligand to stabilize high-valent copper species for the first asymmetric radical oxytrifluoromethylation of alkenes with alcohols under CuI/phosphoric acid dual-catalysis has been developed. The transformation features mild reaction conditions, a remarkably broad substrate scope and excellent functional group tolerance, offering an efficient approach to a wide range of trifluoromethyl-substituted tetrahydrofurans bearing an α-tertiary stereocenter with excellent enantioselectivity. Mechanistic studies support the presumed role of the achiral pyridine as a coordinative ligand on copper metal to stabilize the key transient reaction species involved in the asymmetric induction process.

Polymer anchored 3-benzoyl-1-(1-benzylpiperidin-4-yl)-2-thiopseudourea-Pd(II) complex: An efficient catalyst for the copper and solvent free Sonogashira cross-coupling reaction

An efficient copper and solvent free Sonogashira cross-coupling reaction catalyzed by polymer supported 3-benzoyl-1-(1-benzylpiperidin-4-yl)-2-thiopseudourea-Pd(II) complex 4 (PS-bpt-Pd) was reported. This inexpensive and simply synthesized heterogeneous catalyst 4 afforded excellent yields of the cross-coupling products under mild reaction conditions. We have achieved high yields for aryl iodide coupling reactions with terminal alkynes at room temperature under copper and solvent-free conditions. In addition, we also observed moderate to good yields for aryl bromides as coupling partner. This insoluble PS-bpt-Pd(II) catalyst 4 can be easily recovered by simple filtration and reused up to five times with stable catalytic activity. In addition to this, heterogeneous Pd (II) complex is even applicable on a gram scale for cross-coupling with high catalytic efficiency.

Small-molecular luminous material with 1,2-diphenyl acetylene as acceptor unit, and preparation and application thereof

The invention belongs to the technical field of luminous materials and discloses a small-molecular luminous material with 1,2-diphenyl acetylene as an acceptor unit, and preparation and applications thereof. The preparation method includes the steps of adding the 1,2-diphenyl acetylene compound, a nitrogen-containing compound and a catalyst into a reaction container filled with a solvent under protection of an inert gas; performing a heated stirring reaction, cooling and extracting a reaction product, and spin-drying an organic phase and performing chromatography to obtain the small-molecular luminous material with the 1,2-diphenyl acetylene as the acceptor unit. The small-molecular luminous material has single structure and definite molecular weight, achieves intramolecular charge transfer and solves a problem of unbalanced charge carriers in a mono-polar luminous material, simplifies device structure and improves device performance. The luminous material is used in organic light-emitting devices.