106456-92-2

Upstream product

• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 105-07-7 4-cyanobenzaldehyde 
• 6283-10-9 2-(4-chlorophenyl)-5,5-dimethyl-1,3-dioxane 
• 86164-70-7 2-methyl-2-phenylmalononitrile 
• 1129-35-7 4-cyanobenzoic acid methyl ester 
• 251989-43-2 5,5-dimethyl-2-(4-methylsulfanylphenyl)-1,3-dioxane 
• 557-21-1 zinc(II) cyanide 

Downstream Products

• 106456-88-6 4-(5,5-dimethyl-1,3-dioxan-2-yl)benzaldehyde 
• 138536-82-0 4-(5,5-dimethyl-1,3-dioxan-2-yl)benzylamine 
• 138536-83-1 N-hexyl-N'<(4-formylphenyl)methyl>1,2:4,5-benzenebis(dicarboximide) 
• 136296-58-7 2-Hexyl-6-[4-((1Z,4Z,9Z,15Z)-2,8,12,18-tetrahexyl-3,7,13,17-tetramethyl-15-p-tolyl-porphyrin-5-yl)-benzyl]-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 
• 1612763-91-3 methyl 3-(4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl)-5-methyl-1-phenyl-1H-pyrazole-4-carboxylate 

Relevant academic research and scientific papers

Nickel-Catalyzed Cyanation of Aryl Thioethers

A nickel-catalyzed cyanation of aryl thioethers using Zn(CN)2 as a cyanide source has been developed to access functionalized aryl nitriles. The ligand dcype (1,2-bis(dicyclohexylphosphino)ethane) in combination with the base KOAc (potassium acetate) is essential for achieving this transformation efficiently. This reaction involves both a C-S bond activation and a C-C bond formation. The scalability, low catalyst and reagents loadings, and high functional group tolerance have enabled both late-stage derivatization and polymer recycling, demonstrating the reaction's utility across organic chemistry.

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation

Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.

New Br?nsted-Lewis acidic quaternary ammonium ionic liquids: Synthesis, acidity determination and acidity-catalytic activity relationship

A series of new Br?nsted-Lewis acidic ionic liquids, which are operational simplicity, high stability, low cost and applicable for scaling up, have been synthesized and their activity for acetalization was examined. The comprehensive studies on the acidity-catalytic performance relationship of the Br?nsted-Lewis acidic ionic liquids were performed. IR spectroscopy results confirmed that the new Br?nsted-Lewis acidic ionic liquids possess both Br?nsted and Lewis acid sites. The acidities were determined by Hammett method, and further studies on acidity-activity relationship revealed that the acidity played a key role in the acid-catalyzed probe reactions.

Rapid assessment of protecting-group stability by using a robustness screen

An experimentally simple method has been developed to rapidly establish the stability of widely utilized silyl, acetal, and carbamate protecting groups to a given set of reaction conditions. Assessment of up to twelve protecting groups in a single experiment has been demonstrated. Evaluation of this protocol in two unrelated synthetic transformations suggests that this method can be used to select appropriate protecting groups in the design of synthetic routes.

Facile aldolization catalyzed by ionic liquid [4-sulfbmpyrazine][BF 4]

The acidic functionalized ionic liquid 1-(4-sulfonic group)butyl-3- methylpyrazine tetrafluoroborate (abbreviated as [4-sulfbmpyrazine][BF 4]) was employed as the catalyst of the condensation of aromatic aldehyde and diols. The optimized condition was as follows: aromatic aldehyde (0.20 mol), diols (0.30 mol) and [4-sulfbmpyrazine][BF4] (0.60 g) were refluxed in cyclohexane (10.00 mL) for 1 h. A series of aromatic aldehydes were studied and afforded the corresponding acetals products with good yields which were from 70.3 to 96.9 %. The ionic liquid catalyst could be recycled for four times without significant loss of catalyst reactivity.

Synthesis and Fluorescence Properties of Selectively Metallated Diporphyrins with Electron-Accepting Moieties

Synthesis of selectively metallated diporphyrins with electron-accepting moieties is described.Steady-state fluorescence spectra of these compounds showed substantial quenching of the fluorescence of the free-base porphyrin.A possible "superexchange" mechanism of long-range electron transfer is discussed.

Rothemund and Adler-Longo Reactions Revisited: Synthesis of Tetraphenylporphyrins under Equilibrium Conditions

We present a new synthetic strategy for preparing tetraphenylporphyrins that should greatly expand synthetic entries into porphyrin containing model systems.Pyrrole and the desired benzaldehyde react reversibly at room temperature with trace acid catalysis to form the cyclic tetraphenylporphyrinogen at thermodynamic equilibrium.An oxidant is then added to irreversibly convert the porphyrinogen to the porphyrin.The greater stability of the cyclic porphyrinogen over the open-chain polypyrrylmethanes occurs when the reaction is performed at moderate dilution (10-2 M).The reaction at high dilution or high concentration affords a negligible yield of the cyclic porphyrinogen.Porphyrinogen exchange reactions provide proof of equilibrium.This methodology is complementary to the Adler-Longo procedure, allowing small quantities of porphyrins to be prepared from sensitive aldehydes in 30-40percent yield without difficult purification problems.This methodology is also extended to the preparation of meso-tetraalkylporphyrins and one hybrid porphyrin containing both aryl and alkyl substituents.The mild reaction conditions and convenience of this method permit consideration of new design strategies in preparing complex porphyrins.