433216-33-2

Upstream product

• 123-75-1 pyrrolidine 
• 104-53-0 3-phenyl-propionaldehyde 
• 2942-58-7 diethyl cyanophosphonate 
• 477531-68-3 C₉H₁₆BN₃ 
• 7677-24-9 trimethylsilyl cyanide 
• 121054-03-3 2-hydroxy-4-phenylbutanenitrile 

Downstream Products

• 151647-54-0 3-phenyl-1-pyrrolidin-1-yl-propane-1-one 

Relevant academic research and scientific papers

A Highly Active System for the Metal-Free Aerobic Photocyanation of Tertiary Amines with Visible Light: Application to the Synthesis of Tetraponerines and Crispine A

A highly efficient metal-free catalytic system for the aerobic photocyanation of tertiary amines with visible light is reported. The use of air as terminal oxidant offers an improved safety profile compared with pure oxygen, the used compact fluorescent lamp (CFL) light sources are highly economical, and no halogenated solvents are required. This system not only proves to be effective for a wide variety of trialkylamines, pharmaceuticals, and alkaloids but remarkably also allows the lowest catalyst loading (0.00001 mol % or 0.1 ppm) ever reported for an organic dye. Bruylants reactions and C-alkylation/decyanations were performed on the obtained α-aminonitriles to demonstrate the postfunctionalization of complex molecules. The catalytic system is furthermore applied in the short and effective syntheses of the alkaloids (±)-crispine A and the tetraponerines T7 and T8.

Redox-neutral α-cyanation of amines

α-Aminonitriles inaccessible by traditional Strecker chemistry are obtained in redox-neutral fashion by direct amine α-cyanation/N-alkylation or alternatively, α-aminonitrile isomerization. These unprecedented transformations are catalyzed by simple carboxylic acids.

Al-MCM-41 catalyzed three-component Strecker-type synthesis of α-aminonitriles

Mesoporous aluminosilicate (Al-MCM-41) efficiently catalyzed the three-component Strecker-type reaction of benzylacetone and aniline with trimethylsilyl cyanide in CH2Cl2 at room temperature to afford the corresponding α-aminonitrile in excellent yields (up to 97%). Mesoporous silica (MCM-41), amorphous SiO2-Al2O3, and H-Y and H-ZSM-5 zeolites also catalyzed this reaction, but gave the desired product in lower yields. The Al-MCM-41 catalyzed three-component Strecker-type reaction was applicable to a wide range of ketones, aldehydes, and amines. Furthermore, the Al-MCM-41 catalyst could be applied to a fixed-bed flow reactor: The desired α-aminonitrile derivative was constantly produced in nearly 80% yields for 48 h.

A New and Practical Procedure for the Bruylants Reaction. Zinc-Mediated Synthesis of Tertiary Homoallylamines and β-Aminoesters

N,N-Disubstituted α-aminonitriles undergo Bruylants reaction under Barbier and Reformatsky conditions with activated halides, in the presence of zinc and 10 mol% HOAc. The high yields and the simple operational conditions make this reaction an appealing, approach to N,N-disubstituted homoallylamines and β-aminoesters.

A novel oxidative transformation of α-aminonitriles to amides

A novel oxidative transformation of α-aminonitriles to amides is reported. Oxidation of α-aminonitriles with peracid, followed by basic treatment affords, amides in good yields. A mechanistic aspect of this transformation is also discussed.