429689-40-7

Upstream product

• 536-74-3 phenylacetylene 
• 540-37-4 p-aminoiodobenzene 
• 100-39-0 benzyl bromide 
• 122-85-0 para-acetamidobenzaldehyde 
• 1942-30-9 4-(phenylethynyl)nitrobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 1849-25-8 4-phenylethynylphenylamine 
• 834-24-2 4-[(1Z)-2-phenylethenyl]benzeneamine 
• 108-24-7 acetic anhydride 
• 110-86-1 pyridine 

Downstream Products

• 841-18-9 (E)-1-(4-acetamidophenyl)-2-phenylethene 

Relevant academic research and scientific papers

A mild chemoselective Ru-catalyzed reduction of alkynes, ketones, and nitro compounds

The chemoselective reduction of alkyne, ketones, or nitro groups using (Ph3P)3RuCl2 as an inexpensive catalyst and Zn/water as a stoichiometric reductant is reported. Depending on the nature of the additive and the temperature, good chemoselectivities were observed allowing, e.g., for the selective reduction of a nitro group in the presence of a ketone or an alkyne.

A Solid-Phase Assisted Flow Approach to In Situ Wittig-Type Olefination Coupling

Described herein is the development of a continuous flow, solid-phase triphenylphosphine (PS-PPh3) assisted protocol to facilitate the in situ coupling of reciprocal pairs of halogen and carbonyl functionalised molecular pairs by a Wittig olefination within 15 mins. The protocol entails injecting a single solution (1 : 1 CHCl3 : EtOH) containing the halogenated and carbonyl-based substrates into a continuously flowing stream of CHCl3 : EtOH (1 : 1), passed through a fixed bed of K2CO3 and PS-PPh3. With advancement to the previous PS-PPh3 coupling procedures, the method employs a traditional polystyrene-based immobilisation matrix, the substrate scope of the protocol extended to substituted ketones, secondary alkyl chlorides, and an unprotected maleimide scaffold.

Ligand-free (: Z)-selective transfer semihydrogenation of alkynes catalyzed by in situ generated oxidizable copper nanoparticles

Herein, we present (Z)-selective transfer semihydrogenation of alkynes based on in situ generated CuNPs in the presence of hydrogen donors, such as ammonia-borane and a green protic solvent. This environmentally friendly method is characterized by operational simplicity combined with high stereo- and chemoselectivity and functional group compatibility. Auto-oxidation of CuNPs after the completion of a semihydrogenation reaction results in the formation of a water-soluble ammonia complex, so that the catalyst may be reused several times by simple phase-separation with no need for any special regeneration processes. Formed NH4B(OR)4 can be easily transformed back into ammonia-borane or into boric acid. In addition, a one-pot tandem sequence involving a Suzuki reaction followed by semihydrogenation was presented, which allows minimization of chemical waste production.

Stereoselective Alkyne Hydrogenation by using a Simple Iron Catalyst

The stereoselective hydrogenation of alkynes constitutes one of the key approaches for the construction of stereodefined alkenes. The majority of conventional methods utilize noble and toxic metal catalysts. This study concerns a simple catalyst comprised of the commercial chemicals iron(II) acetylacetonate and diisobutylaluminum hydride, which enables the Z-selective semihydrogenation of alkynes under near ambient conditions (1–3 bar H2, 30 °C, 5 mol % [Fe]). Neither an elaborate catalyst preparation nor addition of ligands is required. Mechanistic studies (kinetic poisoning, X-ray absorption spectroscopy, TEM) strongly indicate the operation of small iron clusters and particle catalysts.

Stereodivergent Alkyne Reduction by using Water as the Hydrogen Source

A homogeneous Pd-catalyzed stereodivergent reduction of alkynes to Z and E alkenes by using H2O as the H2 source is presented. Mediated by a diboron reagent, the transfer hydrogenation has been accomplished to yield the desired geometrical isomer by rational ligand selection. The switchable stereoselectivity achieved using simple phosphine ligands is generally excellent. D2O has also been used as a D2 source for synthesizing the corresponding deuterated olefins. Supported by a gram-scale synthesis, the reaction can easily be scaled up making it an efficient way to prepare alkenes commercially as well. Mechanistic studies suggest formation of H?PdL2?OAc as the crucial step leading to the presence of two pathways involving H?Pd?B(OR)2 and molecular H2 as active intermediates.

Aryl-aryl interactions as directing motifs in the stereodivergent iron-catalyzed hydrosilylation of internal alkynes

The defined Fe hydride complex FeH(CO)(NO)(Ph3P)2 is highly active as a catalyst for selective hydrosilylation of internal alkynes to vinylsilanes. Depending on the silane employed either E- or Z-selective hydrosilylation products were formed in excellent yields and good to excellent stereoselectivities.