Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts

Balaguez, Renata A.; Ricordi, Vanessa G.; Freitas, Camilo S.; Perin, Gelson; Schumacher, Ricardo F.; Alves, Diego

doi:10.1016/j.tetlet.2013.12.086

Cited by 24 publications

(16 citation statements)

References 40 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The combined organic layer was dried by anhydrous Na 2 SO 4 . After distillation of the solvent, the residue was purified by column chromatography (eluent: petroleum ether) to give 5.68 g PhSePh (81% yield) …”

Section: Methodsmentioning

confidence: 99%

Recyclable 1,2‐bis[3,5‐bis(trifluoromethyl)phenyl]diselane‐catalyzed oxidation of cyclohexene with H₂O₂: a practical access to trans‐1,2‐cyclohexanediol

Wang

Chen

et al. 2014

Applied Organom Chemis

View full text Add to dashboard Cite

1,2-Bis[3,5-bis(trifluoromethyl)phenyl]diselane-catalyzed oxidation of cyclohexene by hydrogen peroxide affords a quick, clean and practical access to the important compound trans-1,2-cyclohexanediol under mild conditions. The highly atom-economic properties, clean procedures, high reaction concentration, short reaction time, mild conditions and eco-friendly, recyclable and low loading catalysts facilitate this methodology for possible future practical industrial production.

show abstract

Section: Methodsmentioning

confidence: 99%

Recyclable 1,2‐bis[3,5‐bis(trifluoromethyl)phenyl]diselane‐catalyzed oxidation of cyclohexene with H₂O₂: a practical access to trans‐1,2‐cyclohexanediol

Wang

Chen

et al. 2014

Applied Organom Chemis

View full text Add to dashboard Cite

show abstract

“…Balaguez et al recently described a simple and catalyst-free method to synthesize diaryl selenides. 12 The new method obtained diaryl selenides in moderate to good yields via a direct nucleophilic aromatic substitution reaction of arenediazonium tetrafluoroborate salts and arylselenols in the presence of H 3 PO 2 . …”

Section: (G) Catalyst-free Synthesis Of Diaryl Selenidesmentioning

confidence: 99%

Hypophosphorous Acid

Gao

2014

Synlett

View full text Add to dashboard Cite

Kai Gao was born in 1987 and raised in Huanggang City, Hubei Province, China. He received his degree in chemistry from Hubei University of Science and Technology in 2012. Currently, he is carrying out research under the supervision of Prof. Bo Yang and Dr. Xiali Liao at the Kunming University of Science and Technology. His research focuses on the synthesis of novel phosphoramide ligands and small molecules with important bioactivities.

show abstract

“…4‐Chlorophenyl 4‐Methoxyphenyl Selenide (3ac): Following the general procedure, compound 3ac was obtained from 4‐methoxyphenylhydrazine hydrochloride ( 1a ; 87 mg, 0.5 mmol) and 4,4′‐dichlorodiphenyl diselenide ( 2c ; 95 mg, 0.25 mmol). Purification by preparative TLC (hexane/EtOAc) afforded 3ac (59 mg, 0.20 mmol) as a yellow solid; 40 % yield; m.p.…”

Section: Methodsmentioning

confidence: 99%

Atom‐Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides

Taniguchi

Murata

Takeda³

et al. 2017

Eur J Org Chem

View full text Add to dashboard Cite

An atom‐economical method for the synthesis of unsymmetrical diaryl selenides from arylhydrazines and stoichiometric amounts of diselenides was developed under mild conditions. The new and facile selenide synthesis involved the use of an inexpensive base in air to form unsymmetrical diaryl selenides in good yields. This C–Se radical arylation of diaryl diselenides was performed by forming aryl radicals from arylhydrazines under oxidative conditions. The formation of a phenyl radical was supported by trapping with 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) in air. Therefore, this synthesis might involve a homolytic aromatic substitution (HAS) mechanism. The synthesis is both low costing and environmentally friendly and, therefore, may be useful for the practical synthesis of unsymmetrical diaryl selenides.

show abstract

Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts

Cited by 24 publications

References 40 publications

Recyclable 1,2‐bis[3,5‐bis(trifluoromethyl)phenyl]diselane‐catalyzed oxidation of cyclohexene with H₂O₂: a practical access to trans‐1,2‐cyclohexanediol

Recyclable 1,2‐bis[3,5‐bis(trifluoromethyl)phenyl]diselane‐catalyzed oxidation of cyclohexene with H₂O₂: a practical access to trans‐1,2‐cyclohexanediol

Hypophosphorous Acid

Atom‐Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides

Contact Info

Product

Resources

About

Simple and catalyst-free method for the synthesis of diaryl selenides by reactions of arylselenols and arenediazonium salts

Cited by 24 publications

References 40 publications

Recyclable 1,2‐bis[3,5‐bis(trifluoromethyl)phenyl]diselane‐catalyzed oxidation of cyclohexene with H2O2: a practical access to trans‐1,2‐cyclohexanediol

Recyclable 1,2‐bis[3,5‐bis(trifluoromethyl)phenyl]diselane‐catalyzed oxidation of cyclohexene with H2O2: a practical access to trans‐1,2‐cyclohexanediol

Hypophosphorous Acid

Atom‐Economical Synthesis of Unsymmetrical Diaryl Selenides from Arylhydrazines and Diaryl Diselenides

Contact Info

Product

Resources

About

Recyclable 1,2‐bis[3,5‐bis(trifluoromethyl)phenyl]diselane‐catalyzed oxidation of cyclohexene with H₂O₂: a practical access to trans‐1,2‐cyclohexanediol

Recyclable 1,2‐bis[3,5‐bis(trifluoromethyl)phenyl]diselane‐catalyzed oxidation of cyclohexene with H₂O₂: a practical access to trans‐1,2‐cyclohexanediol