330156-57-5

Upstream product

• 57341-98-7 4-(phenylethynyl)benzaldehyde 
• 18282-51-4 4-iodo-benzyl alcohol 
• 536-74-3 phenylacetylene 
• 54737-75-6 (4-(phenylethynyl)phenyl)methanol 

Relevant academic research and scientific papers

Electrochemical Proton Reduction over Nickel Foam for Z-Stereoselective Semihydrogenation/deuteration of Functionalized Alkynes

Selective reduction strategies based on abundant-metal catalysts are very important in the production of chemicals. In this paper, a method for the electrochemical semihydrogenation and semideuteration of alkynes to form Z-alkenes was developed, using a simple nickel foam as catalyst and H3O+ or D3O+ as sources of hydrogen or deuterium. Good yields and excellent stereoselectivities (Z/E up to 20 : 1) were obtained under very mild reaction conditions. The reaction proceeded with terminal and nonterminal alkynes, and also with alkynes containing easily reducible functional groups, such as carbonyl groups, as well as aryl chlorides, bromides, and even iodides. The nickel-foam electrocatalyst could be recycled up to 14 times without any change in its catalytic properties.

Copper Nanocrystal Plane Effect on Stereoselectivity of Catalytic Deoxygenation of Aromatic Epoxides

Previous studies have shown that crystal planes of heterogeneous catalysts could display enhanced activity, such that higher turnover or chemoselectivity could be achieved. Here we report an example where the reaction stereoselectivity was significantly affected by the catalyst crystal planes. In copper-catalyzed deoxygenation reaction of aromatic epoxides, copper cubes, wires, and plates gave the olefin products with different cis/trans selectivities, whereas homogeneous copper catalysts showed poor selectivity. Scanning tunneling microscope and density functional theory studies revealed that the different adsorption mode and higher adsorption strength of epoxide oxygen on Cu{100} plane were responsible for the observed variation of selectivity. The copper-catalyzed deoxygenation reaction provided new practical access to cis-olefins from readily available aromatic epoxides. Our work also indicated that nanocrystal catalysts may provide useful stereochemical control in organic reactions.

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.

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.

Semihydrogenation of alkynes in the presence of Ni(0) catalyst using ammonia-borane and sodium borohydride as hydrogen sources

The selective semihydrogenation of terminal and internal alkynes was achieved using complexes of the type [(P-P)Ni(η2-C,C-alkyne)] (P-P = chelating diphospine ligands), which behave as the active catalysts and were generated in situ. Boron-hydride derivatives such as ammonia-borane (AB) or sodium boron hydride (SBH) were used as hydrogen sources. In the case of internal alkynes, the stereoselective formation of cis- or trans-alkenes was achieved in high yields and under mild reaction conditions.