Category Ranking
98%
Total Visits
921
Avg Visit Duration
2 minutes
Citations
20
Article Abstract
Nitrogen transfer from cyanide anion to an aldehyde is emerging as a promising method for the synthesis of aromatic nitriles. However, this method still suffers from a disadvantage that a use of stoichiometric Cu(II) or Cu(I) salts is required to enable the reaction. As we report herein, we overcame this drawback and developed a catalytic method for nitrogen transfer from cyanide anion to an alcohol via the complete cleavage of the C≡N triple bond using phen/Cu O as the catalyst. The present condition allowed a series of benzyl alcohols to be smoothly converted into aromatic nitriles in moderate to high yields. In addition, the present method could be extended to the conversion of cinnamic alcohol to 3-phenylacrylonitrile.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1002/asia.202100776 | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Electrosynthesis of Nitriles from Nitrate and Aldehyde via C≡N Bond Construction.
J Am Chem Soc
August 2025
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai, 200062, China.
Electrocatalytic nitrate reduction offers a promising approach to synthesizing valuable organic nitrogen compounds via C-N coupling, serving as a pivotal solution to the pressing nitrate pollution issue. While significant progress has been made in electrosynthesizing C-N and C═N compounds, the electrosynthesis of nitriles with C≡N bond formation via NO as nitrogen sources remains challenging. Herein, we introduce a novel method for efficient synthesizing nitriles through electrocatalytic coupling of nitrate ions (NO) with aldehydes under ambient conditions, employing ZnO/Sn/SnO as the electrocatalyst.
View Article and Find Full Text PDFNitrilation of carboxylic acids by P/P-catalysis.
Chem Sci
August 2025
Department of Chemistry, MIT 77 Massachusetts Ave. Cambridge MA 02139 USA
A mild and catalytic method for the direct conversion of carboxylic acids into their corresponding nitriles is reported. In contrast to common nitrile preparations that rely on hazardous cyanide and cyanogen precursors, the present protocol employs a P/P-catalyzed 'oxidation-reduction condensation' approach to effect iterative amidation/retro-Ritter reaction of carboxylic acids with 1-phenethylamine. Primary, secondary, tertiary, and aromatic carboxylic acids all undergo nitrilation in synthetically viable yields, including several pharmaceuticals and natural products.
View Article and Find Full Text PDFOn the use of ethylene carbonate as a green solvent in mobile phases.
J Chromatogr A
October 2025
Department of chemistry and biochemistry, University of Texas at Arlington, Arlington, TX, USA. Electronic address:
Dimethyl, diethyl, and propylene carbonate esters are polar aprotic solvents that demonstrated their capability as "green" solvents compared to methanol, acetonitrile or even apolar solvents in mobile phases for liquid chromatography. Ethylene carbonate (EC) has a melting point of 36 °C, so as a solid, it cannot be used as a neat solvent in liquid chromatography. However, its molten state is fully miscible with water and such solutions can be effective liquid chromatographic mobile phases.
View Article and Find Full Text PDFDonor-acceptor (D-A) compounds are particularly important in optoelectronic and biological applications. However, they are normally synthesized in the presence of transition metal catalysts. Herein, we report a metal-free method by a complex-mediated nucleophilic aromatic substitution of aryl nitriles with amines.
View Article and Find Full Text PDFElectro-oxidative amination of benzylic C(sp³)-C(sp³) bonds in aromatic hydrocarbons.
Nat Commun
July 2025
Frontiers Science Center for Transformative Molecules (FSCTM), Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs, School of Chemistry and Chemical Engineering, Zhangjiang Institute for Advanced Study, Shanghai Jiao Tong University, Shanghai, China.
C(sp)-C(sp) amination represents a promising approach for synthesizing various amines, facilitating applications from late-stage scaffold hopping to the degradation of polymers and biomass. However, it remains challenging due to the inertness of the C-C bond and difficulties in controlling regio- and chemo-selectivity. Herein, we report an electro-oxidative benzylic C(sp)-C(sp) amination reaction of aromatic hydrocarbons using nitriles, amides, and sulfonamides as nucleophiles.
View Article and Find Full Text PDF