66558-11-0

Upstream product

• 5707-04-0 Phenylselenyl chloride 
• 1745-81-9 o-Allylphenol 
• 1666-13-3 diphenyl diselenide 

Downstream Products

• 74104-12-4 2,3-dihydro-2-methylenebenzo[b]furan 
• 4265-25-2 2-methylbenzofuran 

Relevant academic research and scientific papers

Time-economical synthesis of selenofunctionalized heterocycles via I2O5-mediated selenylative heterocyclization

A time-economical and robust synthesis of various selenofunctionalized heterocycles was accomplished via I2O5-mediated selenocyclizations of olefins with diselenides. Using this method, 116 selenomethyl-substituted heterocycles were

Electrochemical synthesis of selenyl-dihydrofurans via anodic selenofunctionalization of allyl-naphthol/phenol derivatives and their anti-Alzheimer activity

Herein, we report an eco-friendly, electrosynthetic approach for the intramolecular oxyselenylation of allyl-naphthol/phenol derivatives. This reaction proceeds with 0.2 equiv. of nBu4NClO4 as an electrolyte and Pt working electrodes in an undivided cell,

Preparation of Heterocycles via Visible-Light-Driven Aerobic Selenation of Olefins with Diselenides

The aerobic dehydrogenative cyclization of alkenes with easily accessible diselenides facilitated by visible light is reported. Notably, the features of this transition-metal-free protocol are pronounced efficiency and practicality, good functional group

A mild and efficient procedure for alkenols oxyselenocyclization by using ionic liquids

A mild and efficient procedure for the oxyselenocyclization of unsaturated alcohols by treatment with phenylselenyl chloride using ionic liquids as solvents/catalyzers has been developed. The reaction proceeds instantaneously under mild conditions with ab

Synthesis of indoles, 3,1-benzoxazines, and quinolines from 2-alkenylanilides and active seleniums

The reaction of diphenyl diselenide with [bis(trifluoroacetoxy)iodo]benzene followed by the addition of 2-allylphenol gave 2-phenylselenomethyl-2,3- dihydro-benzofuran in 82% yield. The reaction of phenylselenenyl chloride with N-tosyl-2-isopropenylanilide followed by the addition of m-CPBA afforded N-tosyl-3-methylindole in 68% yield. Interestingly, the reaction of diphenyl diselenide with [bis(trifluoroacetoxy)iodo]benzene followed by the addition of 2-isopropenylaniline gave 4-methyl-4-phenylselenomethyl-2-trifluoromethyl-3,1- benzooxazine in 65% yield. Copyright Taylor & Francis Group.

Ring-Closure Reactions Initiated by the Peroxydisulfate Ion Oxidation of Diphenyl Diselenide

The oxidation of diphenyl diselenide with ammonium peroxydisulfate proceeded cleanly to afford phenylselenium cations and sulfate anions.This is a very simple and efficient method to produce phenylselenium cations in the absence of nucleophilic counterions.This reaction was employed to effect selenium-induced ring closure reactions starting from alkenes containing internal nucleophiles.Thus, unsaturated alcohols and amides, β-diketones and β-keto esters gave the products of phenylselenoetherification.The same process occurred with dienes and unsaturated ketones when the reaction was carried out in the presence of water or methanol, respectively.Unsaturated acids, esters, and imides afforded the phenylselenolactonization products.

ORGANOSELENIUM-INDUCED CYCLIZATIONS IN ORGANIC SYNTHESIS

A number of organoselenium reagents are introduced as efficient initiators of ring closures leading from unsaturated substrates to lactones, cyclic ethers, cyclic thioethers, N-heterocycles and carbocycles.These cyclizations often proceed with high ring selectivity and stereoselectivity and are accompained by the incorporation of the phenylseleno group (PheSe) into the final product.Methods are described for the effective removal of this group (PheSe) by oxidation or reduction achieving unsaturation or saturation.Finally the successful application of this Se-based methodology to the synthesis of stable and biologically active prostacyclins is outlined.Representative experimental procedures are included.

Phenylselenoetherification. A Highly Efficient Cyclization Process for the Synthesis of O- and S-Heterocycles

Phenylselenoetherification, a new cyclization procedure based on organoselenium chemistry, is described in detail.Unsaturated hydroxy and thio compounds were subjected to this new cyclization process to afford a series of phenyl selenoethers and phenyl selenothioethers which were transformed to a variety of heterocyclic systems by reductive or oxidative removal of the selenium group.Applications to the synthesis of muscarine analogues are described.