33534-87-1

Upstream product

• 100-66-3 methoxybenzene 
• 3189-43-3 tetracyanoethylene oxide 
• 696-62-8 para-iodoanisole 
• 109-77-3 malononitrile 
• 30698-32-9 methyl 2-cyano-2-(4-methoxyphenyl) acetate 
• 5446-57-1 2-cyano-2-(4-methoxyphenyl) acetamide 
• 623-12-1 4-chloromethoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 99779-72-3 2-Chloro-2-(4-methoxy-phenyl)-malononitrile 
• 1122-85-6 phenyl cyanate 
• 104-47-2 p-methoxybenzylnitrile 
• 2082-66-8 2-chlorobenzylthiocyanate 
• 86145-17-7 2-(4-Methoxy-phenyl)-2-trimethylsilanyloxy-malononitrile 
• 100-07-2 4-methoxy-benzoyl chloride 

Downstream Products

• 106367-53-7 7-Amino-2-(4-chloro-phenyl)-3-hydroxy-5-imino-6-(4-methoxy-phenyl)-5H-pyrazolo[1,2-a]pyrazol-1-one 
• 106367-52-6 7-Amino-3-hydroxy-5-imino-2,6-bis-(4-methoxy-phenyl)-5H-pyrazolo[1,2-a]pyrazol-1-one 

Relevant academic research and scientific papers

Titanium(III)-Catalyzed Reductive Decyanation of Geminal Dinitriles by a Non-Free-Radical Mechanism

A titanium-catalyzed mono-decyanation of geminal dinitriles is reported. The reaction proceeds under mild conditions, tolerates numerous functional groups, and can be applied to quaternary malononitriles. A corresponding desulfonylation is demonstrated as well. Mechanistic experiments support a catalyst-controlled cleavage without the formation of free radicals, which is in sharp contrast to traditional stoichiometric radical decyanations. The involvement of two TiIII species in the C?C cleavage is proposed, and the beneficial role of added ZnCl2 and 2,4,6-collidine hydrochloride is investigated.

Preparation of O-Protected Cyanohydrins by Aerobic Oxidation of α-Substituted Malononitriles in the Presence of Diarylphosphine Oxides

A mild, reagent-cyanide-free, and efficient synthesis of O-phosphinoyl-protected cyanohydrins from readily available α-substituted malononitriles was realized using diarylphosphine oxides in the presence of O2. Mechanistic studies indicated that in addition to the initial aerobic oxidation of the malononitrile derivative notable features of this process include the formation of a tetrahedral intermediate and a subsequent intramolecular rearrangement. The phosphinoyl-protecting group can be removed by alcoholysis or by reduction with DIBAL-H.

Effect of Substituents on the Bond Strength of Air-Stable Dicyanomethyl Radical Thermochromes

A series of substituted aryl dicyanomethyl radicals were synthesized, and the bonding thermodynamic parameters for self-dimerization were determined from van't Hoff plots obtained from variable-temperature electron paramagnetic resonance and ultraviolet-v

Synthesis of substituted isoquinolines via Pd-catalyzed cross-coupling approaches

Palladium complexes incorporating ligands based on a 1,3,5,7-tetramethyl-2, 4,8-trioxa-6-phosphaadamantanyl scaffold were used to catalyze the arylation of ethyl cyanoacetate, malononitrile, and various ketones. The products from these reactions can be el

A convenient protocol for the synthesis of hindered aryl malononitriles

A technically feasible method has been developed for the synthesis of variety of aryl malononitriles in high yields (70-95%) using the palladium-catalyzed coupling reaction of malononitrile with aryl bromides and chlorides, respectively. The influence a s

Single enantiomer, chiral donor-acceptor metal complexes from bisoxazoline pseudoracemates

Single enantiomer, chiral donor-acceptor metal complexes were synthesized via the self-discriminating zinc(II) complexation of a pseudoracemic mixture of donor/acceptor-substituted bisoxazoline derivatives.

An efficient and mild CuI/L-proline-catalyzed arylation of acetylacetone or ethyl cyanoacetate

The coupling reaction of aryl iodides with acetylacetone or ethyl cyanoacetate under catalysis of CuI/L-proline works at relatively mild conditions to provide 3-aryl-2, 4-pentanediones and α-aryl cyanoacetates in moderate to good yields. Georg Thieme Verlag Stuttgart.

Industrial R&D on catalytic C-C and C-N coupling reactions: A personal account on goals, approaches and results

R&D issues for the application of Pd- and Ni-catalyzed C-C and C-N coupling reactions in the fine chemicals industry are discussed. In a first part, some background is given on industrial R&D and the role of C-C and C-N coupling for preparative applicatio

A convenient and efficient palladium-catalyzed system for cross-coupling of aryl bromides with active methylene compounds

A simply catalytic system containing palladium-phosphine complex, generated in situ from PdCl2/tert-phosphino ligand in pyridine, has been systematically studied in the cross-coupling of bromobenzene with malononitrile or ethyl cyanoacetate anion. The effect of molar ratio of phosphine ligand to PdCl2 on the activity of the coupling was also discussed. It is found that the catalytic system has highly catalytic activity to produce aryl malononitriles and cyanoacetates in considerable yields (67-90%) when the substituted aryl bromides were used as substrates.

A highly efficient catalytic system for cross-coupling of aryl chlorides and bromides with malononitrile anion by palladium carbene complexes

Six imidazolium chlorides (1-6) as precursors of 1,3-diaryl substituted N-heterocyclic carbene ligands were synthesized and evaluated in palladium-catalyzed cross-coupling reactions of aryl chlorides and bromides with malononitrile in the presence of NaH.