5558-92-9

Upstream product

• 67-56-1 methanol 
• 140-29-4 phenylacetonitrile 
• 56751-34-9 2-phenyl-propionitrile anion 
• 100-44-7 benzyl chloride 
• 3333-14-0 2,3-diphenylpropionitrile 
• 74-88-4 methyl iodide 
• 100-39-0 benzyl bromide 
• 1823-91-2 1-phenylethyl cyanide 
• 1352054-90-0 C₁₇H₁₅NO₂ 
• 2094-69-1 benzyl pivalate 
• 108-88-3 toluene 
• 60340-31-0 Ethylsulfanyl-phenyl-acetonitrile 
• 32121-59-8 α-(phenylthio)-benzyl cyanide 
• 40400-13-3 2-Iodobenzyl bromide 

Downstream Products

• 7511-43-5 2,3-diphenyl-2-methylpropionic acid 
• 78141-32-9 2-methyl-1,2-diphenylpentan-3-one 
• 681153-30-0 2-methyl-2,3-diphenylpropanamide 
• 1985-96-2 1,2-diphenyl-2-methylpropane 
• 5814-85-7 1,2-diphenylpropane 

Relevant academic research and scientific papers

Copper-catalyzed radical oxidative C(sp3)–H/C(sp3)–H cross-coupling between arylacetonitriles and benzylic compounds

For the first time, a novel copper-catalyzed direct C(sp3)–H/C(sp3)–H cross-coupling of arylacetonitriles with unactivated benzylic compounds was described, allowing various a-benzylated arylacetonitriles to be readily accessible under base-free conditions. Mechanistic investigations suggested that the reaction proceeds through radical process and the C(sp3)–H cleavage of arylacetonitriles probably is the rate-determining step.

Nickel-Catalyzed α-Benzylation of Arylacetonitriles via C-O Activation

Efficient Ni-catalyzed direct cross-couplings of benzylic alcohol derivatives with arylacetonitriles via C-O activation are described. Various α-benzylated arylacetonitriles including those with functional groups can be prepared under mild reaction conditions.

Decarboxylative benzylation and arylation of nitriles

Decarboxylative benzylation of nitriles is achieved via coupling of metallated nitriles with Pd-π-benzyl complexes that are generated in situ from cyanoacetic benzyl esters. In addition, decarboxylative couplings of α,α-disubstituted 2-methylfuranyl cyano

Lithium naphthalenide-induced reductive alkylation and addition of aryl-and heteroaryl-substituted dialkylacetonitriles

Lithium naphthalenide (LN)-induced reductive alkylation/addition reactions of aryl-, pyridyl-, and 2-thienyl-substituted dialkylacetonitriles have been investigated. Upon treatment with LN in THF at -40°C, both aryl and pyridyl precursors could undergo the reductive decyanation smoothly, and the in situ generated carbanions could be readily trapped by alkyl halides, ketones, aldehydes, or even oxygen to afford a wide range of functionalized aromatic derivatives bearing a newly established quaternary carbon. To effect the desired reductive alkylation of 2-thienyldialkylacetonitriles, a much lower temperature such as -100°C was required. Also with these substrates, an interesting ring-opening/S-alkylation process was observed when the reductive alkylation were performed at -78°C to give 1-alkylsulfanyl-1,3,4-trienes. A mechanistic discussion is given for this observation.

Platinum-Catalyzed Selective Hydration of Hindered Nitriles and Nitriles with Acid- or Base-Sensitive Groups

Hindered tertiary nitriles can be hydrolyzed under neutral and mild conditions to the corresponding amides using platinum(II) catalysts with dimethylphosphine oxide or other secondary phosphine oxides (SPOs, phosphinous acids) as ligands. We have found that this procedure also works well for nitriles with acid- or base-sensitive groups, which is unprecedented in terms of yield and selectivity. The catalyst loading can be as low as 0.5 mol %. Amides are isolated as the only product in high yield, and no further hydrolysis to the corresponding acids takes place. Reactions are carried out at 80 °C but take place even at room temperature. When enantiopure secondary phosphine oxide ligands are used in the hydrolysis of racemic nitriles, no kinetic resolution is observed, presumably due to racemization of the ligand during the reaction.

Carbopalladation of nitriles: Synthesis of benzocyclic ketones and cyclopentenones via Pd-catalyzed cyclization of ω-(2-iodoaryl)alkanenitriles and related compounds

An efficient procedure for the synthesis of 2,2-disubstituted benzocyclic ketones by intramolecular carbopalladation of nitriles has been developed. The cyclization of substituted 3-(2-iodoaryl)-propanenitriles affords indanones in high yields. The reaction is compatible with a wide variety of functional groups. This methodology has been extended to the synthesis of tetralones and cyclopentenones.

Oxidative nucleophilic substitution of hydrogen in nitroarenes with phenylacetonitrile derivatives

Tertiary carbanions generated from α-substituted phenylacetonitriles in liquid ammonia add to nitrobenzenes in the para position to form the corresponding σ(H)-adducts which are transformed, depending on the starting nitriles and the reaction conditions, to products of oxidative nucleophilic substitution of hydrogen, ONSH or vicarious nucleophilic substitution, VNS.

THE REDUCTIVE LITHIATION OF THIOACETALS, α,α-BIS(TRIMETHYLSILYL)-ALKYL SULFIDES, AND 2-ALKYL-2-ETHYLTHIOALKANENITRILES USING TRIBUTYLSTANNYLLITHIUM

The reaction of thioacetals of phenyl ketones, α,α-bis(trimethylsilyl)alkyl sulfides, and 2-alkyl-2-ethylthioalkanenitriles with tributhylstannyllithium gave the corresponding α-anions of sulfides, α,α-bis(trimethylsilyl)alkane, and nitriles, respectively.

Steric and Electronic Effects in SN2 reactions of 9-Substituted Fluorenyl and α-Cyano Carbanions with Benzyl Chloride in Dimethyl Sulfoxide Solution

Rates of reactions of PhCH2Cl with carbanions derived from six α-cyano carbon acids of varied structure with pKa values ranging over 16 units have been measured.When placed on a log k vs. pKa plot the points fit near to the extended

OXIDATION OF ALCOHOLS BY TRANSITION METAL COMPLEXES PART V. SELECTIVE CATALYTIC MONOALKYLATION OF ARYLACETONITRILES BY ALCOHOLS

Selective catalytic monoalkylation of arylacetonitriles by primary alcohols can be achieved at o using a catalyst prepared in situ from rhodium trichloride, triphenylphosphine and sodium carbonate.RuH2(PPh3)4 is a more effective catalyst for this process.