52565-72-7

Upstream product

• 5432-07-5 (Z)-3-(4-methoxyphenyl)-2-phenylacrylonitrile 
• 104-47-2 p-methoxybenzylnitrile 
• 14906-59-3 4-cyanopyridine N-oxide 
• 2132-62-9 4,4'-dimethoxydiphenylacetylene 
• 77287-34-4 formamide 
• 104-01-8 4-Methoxyphenylacetic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 693775-74-5 (E)-2,3-bis(4-methoxyphenyl)acrylamide 
• 93330-31-5 4-Methoxy-α-<4-methoxy-phenyl>-trans-zimtsaeurechlorid 
• 32383-67-8 (E)-2,3-bis(4-methoxyphenyl)acrylic acid 

Relevant academic research and scientific papers

Accelerated Discovery of α-Cyanodiarylethene Photoswitches

Cyanodiarylethene chromophores are able to undergo constitutional exchange via dynamic covalent chemistry (DCC). During this process, the central ethylene bridge of the molecular scaffold can be broken and thereby enables the assembly of a new combination of aryl moieties around the reformed ethylene bridge. The reversible CC double bond exchange has exemplarily been investigated using α-cyanostilbenes. Establishing a dynamic equilibrium reaction from α-cyanodiarylethene with arylacetonitriles under mild conditions has been the basis to access constitutional libraries of new photoswitches with potentially improved properties. When subject to irradiation with light of adequate wavelength, α-cyanodiarylethenes undergo Z/E isomerization followed by ring-closure. By screening the thus accessible dynamic chromophore libraries using a desired detection wavelength, we could identify specific dithienyl analogues that exhibit three-state photochromism. The combination of dynamic constitutional libraries of functional chromophores in combination with the light-guided screening and selection should lead to more rapid exploration of structural diversity dye chemistry.

Nickel-Catalyzed Cyanation of Aryl Halides and Hydrocyanation of Alkynes via C-CN Bond Cleavage and Cyano Transfer

We report nickel-catalyzed cyanation and hydrocyanation methods to prepare aryl nitriles and vinyl nitriles from aryl halides and alkynes, respectively. Using inexpensive and nontoxic 4-cyanopyridine N-oxide as the cyano shuttle, the methods provide an efficient approach to prepare aryl cyanides and vinyl nitriles under mild and operationally simple reaction conditions with a broad range of functional group tolerances. In hydrocyanation of alkynes, the method demonstrated good regioselectivity, producing predominantly E- or Z-alkenyl nitriles in a controlled manner and exclusively Markovnikov vinyl nitriles when internal diaryl alkynes and terminal alkynes were applied as the substrates, respectively. The preliminary mechanistic investigation indicated that the C-CN bond cleavage process is promoted by oxidative addition to the nickel(I) complex in the cyanation of aryl halides, and further studies via a series of deuterium exchange experiments indicated that water serves as the hydrogen source for the hydrocyanation of alkynes.

Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions

The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.

Solvent-free condensation of arylacetonitrile with aldehydes

The condensation of a series of arylacetonitriles with aldehydes can be carried out by mixing equivalent amounts of reagents with neat powdered KOH at room temperature for 3-60 min depending on the aldehyde steric hindrance. At higher temperature (110°C), yields were generally higher and purity increased within very short reaction times (1-5 min). With pentamethylphenylacetonitrile, a phase transfer agent was necessary to give a satisfactory yield.

Discovery of Diarylacrylonitriles as a Novel Series of Small Molecule Sortase A Inhibitors

On the basis of a hit from random screening, a novel class of small-molecule sortase A inhibitors was generated. The primary structure-activity relationship and the minimal structural requirements for potency were established through structural modifications and molecular modeling studies.