Unsymmetrical Diorganyl Selenides Research Articles

Preparation of bis(2-pyridyl) diselenide derivatives: Synthesis of selenazolo[5,4-b]pyridines and unsymmetrical diorganyl selenides, and evaluation of antioxidant and anticholinesterasic activities

We describe here an alternative method to prepare bis(2-pyridyl) diselenide derivatives using reduced selenium species, generated in situ, and different 2-chloropyridines promoted by p-TSOH in PEG-400 as solvent. This is a straightforward protocol to prepare bis(3-amino-2-pyridyl) diselenides unprecedented to date. Still, this article describe the employment of synthesized bis(3-amino-2-pyridyl) diselenide and a diverse array of aryl aldehydes to afford the corresponding 2-aryl-selenazolo[5,4-b]pyridines in satisfactory yields and, in a short reaction time under basic condition. Furthermore, when the bis(3-amino-2-pyridyl) diselenide reacted with aliphatic halides, in the presence of NaBH4, a wide range of unsymmetrical diorganyl selenides was obtained. To complete this investigation the bis(3-amino-2-pyridyl) diselenide was evaluated for its inhibitory effect on the acetylcholinesterase (AChE) activity and free radical-scavenging capacity. Results demonstrated that this compound was antioxidant and inhibitor of the AChE activity, being a promising therapeutic agent for the treatment of Alzheimer’s disease and other neurodegenerative disorders.

A highly efficient heterogeneous ruthenium(III)-catalyzed reaction of diaryl diselenides with alkyl halides leading to unsymmetrical diorganyl selenides

A highly efficient heterogeneous ruthenium(III)-catalyzed reaction of diaryl diselenides with alkyl halides was achieved in DMF at 100 °C in the presence of 2 mol% of an MCM-41-immobilized bidentate nitrogen ruthenium(III) complex [MCM-41-2N-RuCl3] and zinc, yielding a variety of unsymmetrical diorganyl selenides in good to excellent yields. This new heterogeneous ruthenium catalyst can easily be prepared via a simple two-step procedure from commercially readily available and inexpensive reagents, and recovered by filtration of the reaction solution and recycled for at least eight times without a significant loss of activity.

ChemInform Abstract: Ionic Liquid: An Efficient and Recyclable Medium for Synthesis of Unsymmetrical Diorganyl Selenides Promoted by InI.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform Abstract: Indium‐Mediated Cleavage of Diphenyl Diselenide and Diphenyl Disulfide: Efficient One‐pot Synthesis of Unsymmetrical Diorganyl Selenides, Sulfides, and Selenoesters.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Indium-mediated cleavage of diphenyl diselenide and diphenyl disulfide: efficient one-pot synthesis of unsymmetrical diorganyl selenides, sulfides, and selenoesters

A convenient and efficient method was developed for the synthesis of alkyl phenyl selenides, sulfides, and selenoesters in one-pot reaction by using indium metal. The reaction showed the selectivity for tert-alkyl, benzylic, and allylic halides over primary and secondary alkyl halides. For the reaction of primary and secondary alkyl iodides and bromides, the yields of selenides were improved by the addition of a catalytic amount of iodine.

Ionic liquid: an efficient and recyclable medium for synthesis of unsymmetrical diorganyl selenides promoted by InI

In an environmentally friendly protocol, InI was used as a reducing agent for the Se-Se bond to prepare unsymmetrical diorganyl selenides with very short reaction times, mild conditions and excellent yields using (bmim)BF(4) as a recyclable solvent.

Efficient synthesis of diorganyl selenides via cleavage of Se–Se bond of diselenides by indium(III) catalyst and zinc

A simple and efficient procedure for the synthesis of unsymmetrical diorganyl selenides from an one-pot indium(III) catalyzed procedure, in the presence of zinc, has been developed. Various organic halides and even the unreactive organic chlorides underwent the reaction efficiently. Also diaryl and dialkyl diselenides underwent the coupling reaction.

Ruthenium(III) Chloride Catalyzed Efficient Synthesis of Unsymmetrical Diorganyl Selenides via Cleavage of Dibenzyl and Diphenyl Diselenides in the Presence of Zinc.

An efficient one-pot route to unsymmetrical diorganyl selenides has been developed by ruthenium(III) chloride catalyzed reactions of dibenzyl or diphenyl diselenides with alkyl halides in the presence of zinc. Organic iodides, bromides, and activated chlorides underwent the reactions efficiently. Unreactive organic chlorides also underwent the same type of selenation with sodium bromide as the additive.

Ruthenium(III) Chloride Catalyzed Efficient Synthesis of Unsymmetrical Diorganyl Selenides via Cleavage of Dibenzyl and Diphenyl Diselenides in the Presence of Zinc

[equation: see text] An efficient one-pot route to unsymmetrical diorganyl selenides has been developed by ruthenium(III) chloride catalyzed reactions of dibenzyl or diphenyl diselenides with alkyl halides in the presence of zinc. Organic iodides, bromides, and activated chlorides underwent the reactions efficiently. Unreactive organic chlorides also underwent the same type of selenation with sodium bromide as the additive.

Indium(I) Iodide‐Promoted Cleavage of Diaryl Diselenides and Disulfides and Subsequent Condensation with Alkyl or Acyl Halides. One‐Pot Efficient Synthesis of Diorganyl Selenides, Sulfides, Selenoesters, and Thioesters.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Indium(I) iodide-promoted cleavage of diaryl diselenides and disulfides and subsequent condensation with alkyl or acyl halides. One-pot efficient synthesis of diorganyl selenides, sulfides, selenoesters, and thioesters.

Diphenyl diselenides and disulfides undergo facile cleavages by indium(I) iodide and the corresponding generated selenate and thiolate anions condense in situ with alkyl or acyl halides present in the reaction mixture. Thus, a simple, efficient, and general procedure has been developed for the synthesis of unsymmetrical diorganyl selenides, sulfides (thioethers), selenoesters, and thioesters by this one-pot reaction at room temperature.

Indium(I) Iodide Mediated Cleavage of Diphenyl Diselenide. An Efficient One‐Pot Procedure for the Synthesis of Unsymmetrical Diorganyl Selenides.

AbstractFor Abstract see ChemInform Abstract in Full Text.

One‐Pot Synthetic Method of Unsymmetrical Diorganyl Selenides: Reaction of Diphenyl Diselenide with Alkyl Halides in the Presence of Lanthanum Metal.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Indium(I) iodide-mediated cleavage of diphenyl diselenide. An efficient one-pot procedure for the synthesis of unsymmetrical diorganyl selenides.

A simple and efficient procedure has been developed for the synthesis of unsymmetrical diorganyl selenides through a one-pot indium(I) iodide-mediated reaction of alkyl halide and diphenyl diselenide in methylene chloride at room temperature. [reaction: see text]

One-pot synthetic method of unsymmetrical diorganyl selenides: reaction of diphenyl diselenide with alkyl halides in the presence of lanthanum metal.

A convenient synthetic method of unsymmetrical selenides has been developed. When diphenyl diselenide was allowed to react with two equimolar amounts of primary alkyl iodides and bromides in the presence of an equimolar amount of lanthanum metal, alkyl phenyl selenides were formed in moderate to good yields. For the reaction of primary alkyl chlorides and secondary alkyl iodides, the yields of the selenides were low; however, the yields were dramatically improved by the addition of TMEDA or HMPA. A reaction pathway involving the generation of a lanthanum phenylselenolate intermediate was suggested.

ChemInform Abstract: Synthesis of α‐Amino Unsymmetrical Diorganyl Selenides via Novel Synthetic Auxiliary Benzotriazole Promoted by Samarium Diiodide.

AbstractChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Synthesis of α-Benzotriazole Selenides and Tellurides Promoted by Samarium Diiodide

Abstract 1-(Benzotriazol-1-yl) unsymmetrical diorganyl selenides and tellurides were synthesized via replacement of chlorine atom in 1-(benzotriazo-l-yl)-l-chloromethane with selenolate and tellurolate anions promoted by SmI2.

Synthesis of α-Amino Unsymmetrical Diorganyl Selenides via Novel Synthetic Auxiliary Benzotriazole Promoted by Samarium Dhodide

Abstract α -Amino unsymmetrical diorganyl selenides are synthesized through nucleophilic substitution of a benzotriazolate anion by selenolates promoted by samarium diiodide.