Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions

Detalhes bibliográficos
Autor(a) principal: Lenardão,Eder J.
Data de Publicação: 2007
Outros Autores: Silva,Márcio S., Mendes,Samuel R., Azambuja,Francisco de, Jacob,Raquel G., Santos,Paulo César Silva dos, Perin,Gelson
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000500011
Resumo: A simple, clean and efficient solvent-free protocol was developed for hydrochalcogenation of alkynes containing a Michael acceptor (ester, ketone and nitrile) with phenylchalcogenolate anions generated in situ from the respective diphenyl dichalcogenide (Se, Te, S), using alumina supported sodium borohydride. This efficient and improved method is general and furnishes the respective (Z)-beta-phenylchalcogeno-<FONT FACE=Symbol>a,b</FONT>-unsaturated esters, ketones and nitriles, in good yield and higher selectivity, compared with those that use organic solvent and inert atmosphere. The use of microwave (MW) irradiation facilitates the procedure and accelerates the reaction.
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spelling Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditionsmicrowave irradiationsolvent-free reactionbeta-phenylchalcogeno estersbeta-phenylchalcogeno ketonesbeta-phenylchalcogeno nitrilesA simple, clean and efficient solvent-free protocol was developed for hydrochalcogenation of alkynes containing a Michael acceptor (ester, ketone and nitrile) with phenylchalcogenolate anions generated in situ from the respective diphenyl dichalcogenide (Se, Te, S), using alumina supported sodium borohydride. This efficient and improved method is general and furnishes the respective (Z)-beta-phenylchalcogeno-<FONT FACE=Symbol>a,b</FONT>-unsaturated esters, ketones and nitriles, in good yield and higher selectivity, compared with those that use organic solvent and inert atmosphere. The use of microwave (MW) irradiation facilitates the procedure and accelerates the reaction.Sociedade Brasileira de Química2007-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000500011Journal of the Brazilian Chemical Society v.18 n.5 2007reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532007000500011info:eu-repo/semantics/openAccessLenardão,Eder J.Silva,Márcio S.Mendes,Samuel R.Azambuja,Francisco deJacob,Raquel G.Santos,Paulo César Silva dosPerin,Gelsoneng2007-10-25T00:00:00Zoai:scielo:S0103-50532007000500011Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2007-10-25T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions
title Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions
spellingShingle Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions
Lenardão,Eder J.
microwave irradiation
solvent-free reaction
beta-phenylchalcogeno esters
beta-phenylchalcogeno ketones
beta-phenylchalcogeno nitriles
title_short Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions
title_full Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions
title_fullStr Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions
title_full_unstemmed Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions
title_sort Synthesis of beta-phenylchalcogeno-alpha, beta-unsaturated esters, ketones and nitriles using microwave and solvent-free conditions
author Lenardão,Eder J.
author_facet Lenardão,Eder J.
Silva,Márcio S.
Mendes,Samuel R.
Azambuja,Francisco de
Jacob,Raquel G.
Santos,Paulo César Silva dos
Perin,Gelson
author_role author
author2 Silva,Márcio S.
Mendes,Samuel R.
Azambuja,Francisco de
Jacob,Raquel G.
Santos,Paulo César Silva dos
Perin,Gelson
author2_role author
author
author
author
author
author
dc.contributor.author.fl_str_mv Lenardão,Eder J.
Silva,Márcio S.
Mendes,Samuel R.
Azambuja,Francisco de
Jacob,Raquel G.
Santos,Paulo César Silva dos
Perin,Gelson
dc.subject.por.fl_str_mv microwave irradiation
solvent-free reaction
beta-phenylchalcogeno esters
beta-phenylchalcogeno ketones
beta-phenylchalcogeno nitriles
topic microwave irradiation
solvent-free reaction
beta-phenylchalcogeno esters
beta-phenylchalcogeno ketones
beta-phenylchalcogeno nitriles
description A simple, clean and efficient solvent-free protocol was developed for hydrochalcogenation of alkynes containing a Michael acceptor (ester, ketone and nitrile) with phenylchalcogenolate anions generated in situ from the respective diphenyl dichalcogenide (Se, Te, S), using alumina supported sodium borohydride. This efficient and improved method is general and furnishes the respective (Z)-beta-phenylchalcogeno-<FONT FACE=Symbol>a,b</FONT>-unsaturated esters, ketones and nitriles, in good yield and higher selectivity, compared with those that use organic solvent and inert atmosphere. The use of microwave (MW) irradiation facilitates the procedure and accelerates the reaction.
publishDate 2007
dc.date.none.fl_str_mv 2007-01-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000500011
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000500011
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532007000500011
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.18 n.5 2007
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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