Hydroselenation of alkynes using NaBH4/BMIMBF4: easy access to vinyl selenides

Lenardão, Eder J.; Dutra, Luiz G.; Saraiva, Maiara T.; Jacob, Raquel G.; Perin, Gelson

doi:10.1016/j.tetlet.2007.09.042

Cited by 26 publications

(8 citation statements)

References 19 publications

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“…We also described the hydroselenation of alkynes 32 starting from diorganyl diselenides 1 using NaBH 4 and [bmim][BF 4 ] as the solvent . This method was extended to several alkynyl alcohols 32 and in all the cases, a mixture of ( Z ) ‐ 37 and gem ‐vinyl selenides 36 was formed.…”

Section: Synthesis Of Vinyl Chalcogenidesmentioning

confidence: 99%

“…For instance, ( Z )‐phenyl(styryl)tellane was obtained selectively in 83 % yield after 1.5 h. The PEG‐400 was reused for successive reactions using phenylacetylene and diphenyl diselenide as starting materials; after four runs using the same solvent, the product was obtained in comparable yields (85‐71 %). In the same work, we studied the reaction of diphenyl diselenide with phenylacetylene using glycerol as the solvent and a mixture of ( E )‐ and ( Z )‐1,2‐bis‐phenylseleno styrenes was formed, i. e., the reaction behavior in glycerol was similar to that using IL or without solvent …”

Section: Synthesis Of Vinyl Chalcogenidesmentioning

confidence: 99%

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Synthesis of Organochalcogen Compounds using Non-Conventional Reaction Media

et al. 2016

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This review is dedicated to the memory of Prof. Nicola Petragnani, a pionner in the chemistry of selenium and tellurium in Brazil, who passed away on December 5, 2015.Organochalcogen compounds (containing S, Se and Te) are interesting either for use as an intermediate in the synthesis of complex molecules or for the exploitation of their biological properties. The growing in the number of papers on the synthesis and application of organochalcogen compounds has been accompanied by a concern about how they are prepared. Here, we provide a comprehensive and updated review on re-cent synthetic methods available for their synthesis using alternative solvents or solvent-free conditions and non-classical energy sources (microwaves irradiation, sonochemistry and mechanochemistry). Organized in fourteen sections, this review brings the more than one hundred alternative methods described so far to access organic compounds containing selenium, tellurium and sulfur.[a] Prof.

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Section: Synthesis Of Vinyl Chalcogenidesmentioning

confidence: 99%

Section: Synthesis Of Vinyl Chalcogenidesmentioning

confidence: 99%

Synthesis of Organochalcogen Compounds using Non-Conventional Reaction Media

et al. 2016

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“…64,65,[66][67][68][69][70][71] Diphenyl selenides can also be achieved by the transition metal-free reaction of sodium selenide and aryl diazonium salts. [72][73][74][75][76][77] In general, to avoid handling of unstable, air/moisture-sensitive, and foul smelling reagents like selenols, diphenyl diselenides are used as starting materials.…”

Section: Metal Nanoparticle-catalyzed Aryl-selenium Bond Formationmentioning

confidence: 99%

Aryl Carbon–Heteroatom Coupling Reactions Using Nanometal Catalyst

Ranu

Saha

Kundu

et al. 2013

Nanocatalysis Synthesis and Applications

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“…In despite of the high versatility of vinyl chalcogenides and the green feature of ILs, their use as solvent for hydrochalcogenation reaction of alkynes was scarcely explored. 33 As a continuation of our studies toward the development of new and cleaner methods for the synthesis of organochalcogenides, [33][34][35][36][37][38][39][40] we report herein the full results on the hydrochalcogenation of alkynes using NaBH 4 and [bmim]BF 4 as recyclable solvent for the synthesis of vinyl selenides and tellurides (Scheme 1).…”

Section: Introductionmentioning

confidence: 99%

NaBH4/[bmim]BF4: a new reducing system to access vinyl selenides and tellurides

Lenardão

Gonçalves

Mendes

et al. 2010

J. Braz. Chem. Soc.

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Um método simples e geral foi desenvolvido para a síntese de selenetos e teluretos vinílicos a partir de alquinos terminais e dicalcogenetos de diorganoíla usando NaBH 4 e [bmim]BF 4 como solvente reciclável. Este método eficiente permite a formação preferencial de calcogenetos vinílicos de configuração Z na maioria dos exemplos estudados. Também foi observado que na reação envolvendo fenilacetileno, (E)-bis-fenilcalcogenoestirenos foram obtidos com bons rendimentos e alta seletividade. O líquido iônico foi reutilizado três vezes sem perda da eficiência.A general and simple method for the synthesis of vinyl selenides and tellurides starting from terminal alkynes and diorganyl chalcogenides using NaBH 4 and [bmim]BF 4 as a recyclable solvent was developed. This efficient and improved method furnishes the corresponding vinyl chalcogenides preferentially with Z configuration. We also observed that when the same protocol was applied to phenyl acetylene, (E)-bis-phenylchalcogeno styrenes were obtained in good yields and high selectivity. The ionic liquid was reused up three times without lost of efficiency.

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Hydroselenation of alkynes using NaBH4/BMIMBF4: easy access to vinyl selenides

Cited by 26 publications

References 19 publications

Synthesis of Organochalcogen Compounds using Non-Conventional Reaction Media

Synthesis of Organochalcogen Compounds using Non-Conventional Reaction Media

Aryl Carbon–Heteroatom Coupling Reactions Using Nanometal Catalyst

NaBH4/[bmim]BF4: a new reducing system to access vinyl selenides and tellurides

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