70102-88-4

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 75-05-8 acetonitrile 
• 1446698-46-9 (dimethylsilyl)acetonitrile 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 5765-44-6 5-methylisoxazole 
• 100-39-0 benzyl bromide 

Relevant academic research and scientific papers

A robust nickel catalyst for cyanomethylation of aldehydes: Activation of acetonitrile under base-free conditions

Nick of time: The nickel cyanomethyl complex 1 catalyzes the room temperature coupling of aldehydes with acetonitrile under base-free conditions. The catalytic system is long-lived and remarkably efficient with high turnover numbers (TONs) and turnover fr

Nucleophilic addition of α-(dimethylsilyl)nitriles to aldehydes and ketones

α-Alkylated (dimethylsilyl)acetonitriles (Me2HSiCR 3R4CN) react spontaneously with aldehydes in DMSO to give β-hydroxynitriles in good to high yields. The addition to ketones is effectively promoted by using MgCl2/su

N-Heterocyclic carbene-catalyzed cyanomethylation of aldehydes with TMSAN

N-Heterocyclic carbenes (NHCs) have been served as efficient catalysts for cyanomethylation of carbonyl compounds. In the presence of 5 mol % NHC, various aldehydes and 2,2,2-trifluoroacetophenone reacted with trimethylsilylacetonitrile (TMSAN) to give β-hydroxynitriles in moderate to high yields.

Metal or ammonium alginates as Lewis base catalysts for the 1,2-addition of silyl nucleophiles to carbonyl compounds

Several metal (Na+, Ca2+) or ammonium (n-Bu 4N+) derivatives of alginic acid, an abundant bio-polymer obtained from the cell walls of brown algae, were synthesized. Their potential to act as organocatalysts to catalyze the 1,2-addition of various silyl derivatives to carbonyl compounds was evaluated for the first time. Ammonium alginate 1h is able to promote the reaction in modest to good isolated yields (up to 98%) affording access to a large range of substrates (β-cyano alcohols or ester, β-substituted methylacrylate or acrylonitrile, and cyanohydrin) by using only 5 mol % of catalyst.

Catalytic cyanomethylation of carbonyl compounds and imines with highly basic phosphine

A highly basic phosphine, tris(2,4,6-trimethoxy phenyl)phosphine (TTMPP), catalyzes cyanomethylation using trimethylsilylacetonitrile (TMSCH2CN) to give the corresponding products in good to high yields, with both carbonyl compounds and imines.

Catalytic nucleophilic activation of acetonitrile via a cooperative catalysis of cationic Ru complex, DBU, and NaPF6

The development of an efficient catalytic system for the direct addition of acetonitrile under mild amine basic conditions is described. A cooperative catalysis of CpRu complex, DBU, and NaPF6 enables chemoselective and catalytic generation of

Catalytic chemoselective addition of acetonitrile to enolizable aldehydes with cationic Ru complex/DBU combination

The cooperative catalysis of CpRu(PPh3)2(CH 3CN)PF6 (1b) and DBU enables chemoselective nucleophilic activation of acetonitrile in the presence of base-sensitive aldehydes 2 to afford corresponding β-hydroxynitr

Lewis base-catalyzed cyanomethylation of carbonyl compounds with (trimethylsilyl)acetonitrile

Catalytic cyanomethylation of various carbonyl compounds with (trimethylsilyl)acetonitrile (TMSCH2CN) in the presence of Lewis bases such as cesium or lithium acetate proceeded smoothly to afford the corresponding cyanomethylated adducts in good yields. Copyright

Thiacrown Ether Technology in Lipase-Catalyzed Reaction: Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomehtyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.

Enhanced Enantioselectivity of an Enzymatic Reaction by the Sulfur Functional Group. A Simple Preparation of Optically Active β-Hydroxy Nitriles Using a Lipase

The enantioselectivity of a lipase-catalyzed hydrolysis was improved by varying the acyl residue into the sulfur functional one, i.e. the β-(phenylthio)- or β-(methylthio)acetoxy group, from acetate or valerate to realize satisfactory resolution of β-hydr