5439-39-4

Usage

Synthesis Reference(s)

Tetrahedron Letters, 29, p. 2261, 1988 DOI: 10.1016/S0040-4039(00)86727-1

InChI:InChI=1/C12H8N2/c13-9-12(10-14)8-4-7-11-5-2-1-3-6-11/h1-8H/b7-4+

Upstream product

• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 104-54-1 3-Phenylpropenol 
• 14371-10-9 (E)-3-phenylpropenal 
• 141-52-6 sodium ethanolate 
• 109-77-3 malononitrile 

Downstream Products

• 489434-09-5 2,2,3,3-Tetramethoxy-4-((E)-styryl)-cyclobutane-1,1-dicarbonitrile 
• 489433-99-0 2,2,3,3-Tetraethoxy-4-((E)-styryl)-cyclobutane-1,1-dicarbonitrile 
• 1221564-19-7 4-[2-amino-3-cyano-4-styryl-5-oxo-5,6,7,8-tetrahydroquinolin-1(4H)-yl]benzenesulfonamide 

Relevant academic research and scientific papers

One-pot oxidant-free dehydrogenation-Knoevenagel tandem reaction catalyzed by a recyclable magnetic base-metal bifunctional catalyst

A new base-metal bifunctional catalyst NH-Pd(0)@MNP was prepared via a facile procedure and fully characterized. The as-prepared catalyst was used as an efficient relay catalyst for the one-pot oxidant-free dehydrogenation-Knoevenagel condensation tandem reaction from benzyl alcohol in H2O under mild conditions and generated benzalmalononitriles with yield up to 96%. Meanwhile, the catalyst could be easily recovered from the reaction system by an external magnetic field, and is reusable with little loss of activity up to 6 runs (5%).

Tungstate-loaded triazine-based magnetic poly(Bis-imidazolium ionic liquid): An effective bi-functional catalyst for tandem selective oxidation/Knoevenagel condensation in water

A novel bi-functional polymeric catalyst was synthesized by immobilization of tungstate anions onto the nitrogen rich poly(ionic liquid)/magnetic nanocomposite. The resulting catalyst has two types of catalytic sites: (i) immobilized WO4 anions with bis-imidazolium ionic liquid cation for selective oxidation of alcohols and (ii) basic amine groups for Knoevenagel condensation between produced aldehyde and malononitrile. Due to the polymeric nature of the catalyst, large amounts of tungstate and basic nitrogen groups were presented on the solid surface which led to a decrease in the applied catalyst mass for catalytic reaction. High catalytic activity and excellent selectivity of catalyst in water medium make this protocol a green way for production of fine chemicals.

H3PW12O40/mpg-C3N4 as an efficient and reusable bifunctional catalyst in one-pot oxidation-Knoevenagel condensation tandem reaction

A single-site bifunctional catalyst for the oxidation-Knoevenagel condensation tandem reaction was prepared by the immobilization of phosphotungstic acid (HPW) on mesoporous graphitic carbon nitride (mpg-C3N4) via electrostatic interaction (HPW/mpg-C3N4). The results of Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), solid-state 31P nuclear magnetic resonance (solid-state 31P NMR), zeta potentials, X-ray photoelectron spectroscopy (XPS) and thermogravimetric analysis (TGA) demonstrated that HPW was successfully immobilized on the protonated mpg-C3N4 by electrostatic interaction. The acid amounts of the catalysts were determined by NH3 temperature programmed desorption (NH3-TPD). The textural properties and morphology of HPW/mpg-C3N4 were characterized by N2 adsorption-desorption, scanning electron microscopy (SEM) and transmission electron microscopy (TEM). 30% HPW/mpg-C3N4 shows the best catalytic performance in the tandem reaction with 98.4% benzyl alcohol conversion and 96.2% selectivity to benzylidene malononitrile. The excellent catalytic performance of 30% HPW/mpg-C3N4 in the tandem reaction is due to the good catalytic performance of HPW in the oxidation and Knoevenagel condensation, respectively. Furthermore, protonated mpg-C3N4 not only acts as a support to facilitate good dispersion of HPW but also promotes the Knoevenagel condensation reaction effectively. Moreover, the HPW/mpg-C3N4 catalyst could be recycled easily without significant loss of catalytic activity.

Fluorous bispidine: A bifunctional reagent for copper-catalyzed oxidation and knoevenagel condensation reactions in water

Fluorous bispidine-type ligands have been developed to facilitate its recovery and reusability and to demonstrate its bifunctional property as a ligand and base in copper-catalyzed aerobic oxidation, the Knoevenagel condensation and tandem oxidation/Knoevenagel condensation in water under mild conditions. Application of the fluorous ligand was also extended to the surfactant-free copper-catalyzed allylic and benzylic sp3 C-H oxidation reaction in water. The fluorous ligands could be recovered using F-SPE with recovery ranging from 91-97% and could be reused five times with little loss of activity.