36735-42-9

Upstream product

• 108-24-7 acetic anhydride 
• 104-85-8 para-methylbenzonitrile 
• 105-07-7 4-cyanobenzaldehyde 

Downstream Products

• 21388-95-4 4-cyanobenzyl acetate 
• 61973-88-4 E,E-2,6-bis(4-cyanostyryl)pyridine 
• 27242-36-0 (E)-4-[2-(6-methylpyridin-2-yl)vinyl]benzonitrile 
• 6051-41-8 4-formylbenzamide 
• 105-07-7 4-cyanobenzaldehyde 

Relevant academic research and scientific papers

Selective Synthesis of Acylated Cross-Benzoins from Acylals and Aldehydes via N-Heterocyclic Carbene Catalysis

The utility of acylals as building blocks for selective cross-benzoin synthesis was explored in this study. The synthesis of α-acetoxyketones (O-acyl cross-benzoins) was achieved via selective N-heterocyclic carbene-catalyzed cross-benzoin reactions using acylals as aldehyde equivalents. Thus, the combination of ortho-substituted phenyl acylals and aromatic/aliphatic aldehydes as coupling substrates using bicyclic triazolium salts as precatalysts and potassium carbonate as a base in THF at reflux temperature selectively yielded O-acyl cross-benzoins.

Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents

A variety of functionalized triarylmethane and 1,1-diarylalkane derivatives were prepared via a transition-metal-free, one-pot and two-step procedure, involving the reaction of various benzal diacetates with organozinc reagents. A sequential cross-coupling is enabled by changing the solvent from THF to toluene, and a two-step SN1-type mechanism was proposed and evidenced by experimental studies. The synthetic utility of the method is further demonstrated by the synthesis of several biologically relevant molecules, such as an anti-tuberculosis agent, an anti-breast cancer agent, a precursor of a sphingosine-1-phosphate (S1P) receptor modulator, and a FLAP inhibitor.

N-Propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) as a green and reusable heterogeneous nanocatalyst for the chemoselective preparation and deprotection of acylals

Abstract: N-propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) was simply synthesized and used as a highly efficient, environmentally friendly, and chemoselective catalyst for the synthesis of 1,1-diacetates (acylals) from the one-pot condensation reaction of various aromatic aldehydes with acetic anhydride, in high yield of products (86–96%) and short reaction time (20–60?min) under solvent-free conditions at room temperature. In addition to these results, we further studied the possibility of deprotection of the resulting acylals into benzaldehyde derivatives in this catalytic system by the addition of water. More importantly, noteworthy advantages of this study are non-use of toxic organic solvents and catalysts, simple work-up procedure, short reaction time, high yield of products, and recovery and reusability of MNPs-PSA by an external magnet. Graphical Abstract: A simple and highly efficient procedure for the protection of various aldehydes with acetic anhydride in the presence of N-propylsulfamic acid supported onto magnetic Fe3O4 nanoparticles (MNPs-PSA) is reported. We further studied the possibility of deprotection of the resulting acylals into benzaldehyde derivatives in this catalytic system by the addition of water as a green solvent. The catalyst was reused several times without loss of its catalytic activity.

Microwave-assisted green synthesis of 1,1-diacetates (acylals) using selectfluor as an environmental-friendly catalyst under solvent-free conditions

An efficient and simple procedure has been developed for the acetylation of aldehyde by selectfluor [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo[2,2,2]octane bis(tetrafluoroborate)] as a chemoselective and environmentally friendly catalyst under solvent-free conditions or microwave irradiation. The application of microwave irradiation improved the yields and reduced the reaction times. In this study, selective conversion of aldehydes was observed in the presence of ketones, and the deprotection of 1,1-diacetates has also been achieved using selectfluor in water as green solvent in reflux conditions. The methodology provides synergy of microwave irradiation which offers several advantages such the simple work-up procedure, short reaction time, excellent yields and environmentally benign procedure.

Solvent-free Chemoselective Synthesis of 1,1-diacetates Catalyzed by Iron Zirconium Phosphate

In the present study, a mild, rapid, and efficient method for the protection of aldehydes with acetic anhydride (AA) in the presence of iron zirconium phosphate (ZPFe), at room temperature is reported. Selective conversion of aldehydes was observed in the presence of ketones. Under these conditions, different aldehydes bearing electron-withdrawing and electron-donating substituents were reacted with AA and the corresponding 1,1-diacetates (acylals) were obtained in high to excellent yields. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions. Also, the deprotection of 1,1-diacetates has been achieved using this catalyst in water. The catalyst was characterized by several physico-chemical techniques. It was recovered easily from the reaction mixture, regenerated, and reused at least 7 times without significant loss in catalytic activity. This protocol has the advantages of easy availability, stability, reusability of the eco-friendly catalyst, chemoselectivity, simple experimental and work-up procedure, solvent-free conditions and only a stoichiometric amount of AA is needed.

Zinc zirconium phosphate as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions

In the present study, a mild, rapid, and efficient method for the protection of aldehydes with acetic anhydride (AA) in the presence of zinc zirconium phosphate (ZPZn) as a nano catalyst, at room temperature is reported. Selective conversion of aldehydes was observed in the presence of ketones. Under these conditions, different aldehydes bearing electron-withdrawing and electron-donating substituents were reacted with AA and the corresponding 1,1-diacetates (acylals) were obtained in high to excellent yields. The steric and electronic properties of the different substrates had a significant influence on the reaction conditions. Also, the deprotection of 1,1-diacetates has been achieved using this catalyst in water. This nanocatalyst was characterized by several physico-chemical techniques. It was recovered easily from the reaction mixture, regenerated and reused at least 7 times without significant loss in catalytic activity. This protocol has the advantages of easy availability, stability, reusability of the eco-friendliness, chemoselectivity, simple experimental and work-up procedure, solvent-free conditions and usage of only a stoichiometric amount of AA.

Green procedures for the chemoselective synthesis of acylals and their cleavage promoted by recoverable sulfonic acid based nanoporous carbon (CMK-5-SO3H)

A selective synthesis of gem-diacetates from the reaction of aldehydes and acetic anhydride in the presence of recyclable nanoporous solid sulfonic acid (CMK-5-SO3H) under solvent-free reaction conditions is reported. The catalyst was also found to be highly active for deprotection of resulting acylals in water. [Figure not available: see fulltext.]

Poly(4-vinylpyridinium) perchlorate as an efficient solid acid catalyst for the chemoselective preparation of 1,1-diacetates from aldehydes under solvent-free conditions

Poly(4-vinylpyridinium) perchlorate has been used as a supported, recyclable, environmentally-benign catalyst for the formation of acylals from aliphatic and aromatic aldehydes in good to excellent yields under solvent-free conditions. Notably, the reaction conditions were tolerant of ketones. This methodology offers several distinct advantages, including its operational simplicity and high product yield, as well as being green in terms of avoiding the use of toxic catalysts and solvents. Furthermore, the catalyst can be recovered and reused several times without any loss in its activity.

Functionalized Poly(Amidoamine) Dendrimer as a Strong Ionic Br?nsted Acid Organocatalyst for Protection/Deprotection of Aldehydes

Poly(amidoamine) dendrimer (PAMAM) was successfully functionalized by chlorosulfonic acid to form an strong ionic acid catalyst. The resulting polymeric catalyst was shown to be an efficient catalyst for the synthesis of 1,1-diacetyl from aldehydes under free solvent conditions at room temperature. Also, the deprotection of the resulting aldehydes was investigated under catalytic conditions. The Hammett acidity function of catalyst showed that catalyst is a strong Br?nsted acid. Due to the multi-functional nature of PAMAM, the catalyst has high loading level of acidic protons.

Ultrasound assisted the chemoselective 1,1-diacetate protection and deprotection of aldehydes catalyzed by poly(4-vinylpyridinium)hydrogen sulfate salt as a eco-benign, efficient and reusable solid acid catalyst

Poly(4-vinylpyridinium) hydrogen sulfate solid acid was found to be efficient catalyst for preparation of 1,1-diacetate using ultrasound irradiation at ambient temperature and neat condition. Deprotection of the resulting 1,1-diacetates were achieved using the same catalyst in methanol solvent under ultrasound irradiation at room temperature. This new method consistently has the advantage of excellent yields and short reaction times. Utilization of solvent free, simple reaction conditions, isolation, and purification makes this manipulation very interesting from an economic and environmental perspective. Further, the catalyst can be reused and recovered for several times.