67960-88-7

Upstream product

• 23974-72-3 sodium phenylselenide 
• 5500-21-0 cyclopropropanecarbonitrile 
• 1666-13-3 diphenyl diselenide 
• 628-20-6 4-Chlorobutyronitrile 
• 827-54-3 2-naphthylethylene 
• 98-80-6 phenylboronic acid 
• 5332-06-9 4-bromobutanenitrile 

Downstream Products

• 74023-56-6 4-benzeneselenyl-1-butylamine 
• 182635-27-4 1-Methyl-4-phenylselanyl-butylamine 
• 1380434-93-4 C₁₀H₁₂N₄Se 

Relevant academic research and scientific papers

Photoinduced Copper-Catalyzed Asymmetric C-O Cross-Coupling

The construction of carbon-heteroatom bonds is one of the most active areas of research in organic chemistry because the function of organic molecules is often derived from the presence of heteroatoms. Although considerable advances have recently been achieved in radical-involved catalytic asymmetric C-N bond formation, there has been little progress in the corresponding C-O bond-forming processes. Here, we describe a photoinduced copper-catalyzed cross-coupling of readily available oxime esters and 1,3-dienes to generate diversely substituted allylic esters with high regio- and enantioselectivity (>75 examples; up to 95% ee). The reaction proceeds at room temperature under excitation by purple light-emitting diodes (LEDs) and features the use of a single, earth-abundant copper-based chiral catalyst as both the photoredox catalyst for radical generation and the source of asymmetric induction in C-O coupling. Combined experimental and density functional theory (DFT) computational studies suggest the formation of π-allylcopper complexes from redox-active oxime esters as bifunctional reagents and 1,3-dienes through a radical-polar crossover process.

Organocatalytic Three-Component 1,2-Cyanoalkylacylation of Alkenes via Radical Relay

Here, we report an unprecedented regioselective, intermolecular 1,2-cyanoalkylacylation of feedstock alkenes with readily available oxime esters and aldehydes by N-heterocyclic carbene (NHC) organocatalysis. The crux of this success is the exquisite control over the radical relay process by an NHC organocatalyst. This protocol offers a general platform for diversity-oriented synthesis of valuable ketonitriles under mild, transition-metal-free, and redox-neutral conditions and highlights its potential in the late-stage functionalization of pharmaceutical architectures and natural products.

Copper-Catalyzed Radical Cross-Coupling of Redox-Active Oxime Esters, Styrenes, and Boronic Acids

A visible-light-driven, copper-catalyzed three-component radical cross-coupling of oxime esters, styrenes, and boronic acids has been developed. Key steps of this protocol involve catalytic generation of an iminyl radical from a redox-active oxime ester and subsequent C?C bond cleavage to generate a cyanoalkyl radical. Upon its addition to styrene, the newly formed benzylic radical undergoes coupling with a boronic-acid-derived ArCuII complex to achieve 1,1-diarylmethane-containing alkylnitriles.

Synthesis of novel selenium and tellurium-containing tetrazoles: A class of chalcogen compounds with antifungal activity

We describe herein the synthesis and antifungal activity of new 5-arylchalcogenoalkyl-1H-tetrazoles 4. Arylchalcogenoalkyl-1H-tetrazoles 4 have been synthesized in high yields by reaction of arylchalcogenolate anions with chloronitriles 2, and subsequent

Nucleophilic ring opening of mono-activated cyclopropanes with arylselenolates generated from diselenides in the presence of a Zn/AlCl 3 system

An efficient one-pot synthesis of γ-arylselenenyl ketones, acids, and nitriles is presented. The method uses Zn/AlCl3-promoted cleavage of diselenides and subsequent ring-opening of mono-activated cyclopropanes. Georg Thieme Verlag Stuttgart.

Radical cyclisations of imines and hydrazones

Radical cyclisation of sp3 carbon-centred radicals onto imines and hydrazones provides a new method for the synthesis of 5- and 6-membered ring nitrogen heterocycles. Cyclisation onto the electrophilic carbon of the C=N group and 5-exo stereoelectronic selectivity are the dominating mechanistic parameters. The C-centred radical intermediates were generated from benzeneselenyl precursors using Bu3SnH.

Cyclisation of Carbinyl Radicals onto Imines and Hydrazones

The regioselectivity of intramolecular addition of sp3 carbon-centered radicals onto C=N double bonds of imines and hydrazones is influenced by the position and polarisation of the C=N bond.