Bi(OTf)3 or Bi(TFA)3 catalyzed efficient, regio- and chemoselectively synthesis of beta-hydroxy thioethers from aryl disulfides in the presence of zinc powder

Detalhes bibliográficos
Autor(a) principal: Khodaei,Mohammad Mehdi
Data de Publicação: 2005
Outros Autores: Khosropour,Ahmad Reza, Ghozati,Kazem
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=S0103-50532005000400032
Resumo: A new convenient method has been developed for the synthesis of beta-hydroxy thioethers with aryl disulfides and zinc powder in the presence of catalytic amounts of Bi(OTf)3 and Bi(TFA)3 in acetonitrile. The present method is very simple and the conditions tolerate a variety of acid-sensitive protecting groups. On the other hand, alkyl or benzyl disulfides afforded no corresponding thioethers under similar conditions. Then the observed regio- and chemoselectivity can be considered as a noteworthy advantage of this method.
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spelling Bi(OTf)3 or Bi(TFA)3 catalyzed efficient, regio- and chemoselectively synthesis of beta-hydroxy thioethers from aryl disulfides in the presence of zinc powderbeta-hydroxy thioethersepoxidesdisulfidesBi(III) compoundszincA new convenient method has been developed for the synthesis of beta-hydroxy thioethers with aryl disulfides and zinc powder in the presence of catalytic amounts of Bi(OTf)3 and Bi(TFA)3 in acetonitrile. The present method is very simple and the conditions tolerate a variety of acid-sensitive protecting groups. On the other hand, alkyl or benzyl disulfides afforded no corresponding thioethers under similar conditions. Then the observed regio- and chemoselectivity can be considered as a noteworthy advantage of this method.Sociedade Brasileira de Química2005-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000400032Journal of the Brazilian Chemical Society v.16 n.3b 2005reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532005000400032info:eu-repo/semantics/openAccessKhodaei,Mohammad MehdiKhosropour,Ahmad RezaGhozati,Kazemeng2005-08-09T00:00:00Zoai:scielo:S0103-50532005000400032Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2005-08-09T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Bi(OTf)3 or Bi(TFA)3 catalyzed efficient, regio- and chemoselectively synthesis of beta-hydroxy thioethers from aryl disulfides in the presence of zinc powder
title Bi(OTf)3 or Bi(TFA)3 catalyzed efficient, regio- and chemoselectively synthesis of beta-hydroxy thioethers from aryl disulfides in the presence of zinc powder
spellingShingle Bi(OTf)3 or Bi(TFA)3 catalyzed efficient, regio- and chemoselectively synthesis of beta-hydroxy thioethers from aryl disulfides in the presence of zinc powder
Khodaei,Mohammad Mehdi
beta-hydroxy thioethers
epoxides
disulfides
Bi(III) compounds
zinc
title_short Bi(OTf)3 or Bi(TFA)3 catalyzed efficient, regio- and chemoselectively synthesis of beta-hydroxy thioethers from aryl disulfides in the presence of zinc powder
title_full Bi(OTf)3 or Bi(TFA)3 catalyzed efficient, regio- and chemoselectively synthesis of beta-hydroxy thioethers from aryl disulfides in the presence of zinc powder
title_fullStr Bi(OTf)3 or Bi(TFA)3 catalyzed efficient, regio- and chemoselectively synthesis of beta-hydroxy thioethers from aryl disulfides in the presence of zinc powder
title_full_unstemmed Bi(OTf)3 or Bi(TFA)3 catalyzed efficient, regio- and chemoselectively synthesis of beta-hydroxy thioethers from aryl disulfides in the presence of zinc powder
title_sort Bi(OTf)3 or Bi(TFA)3 catalyzed efficient, regio- and chemoselectively synthesis of beta-hydroxy thioethers from aryl disulfides in the presence of zinc powder
author Khodaei,Mohammad Mehdi
author_facet Khodaei,Mohammad Mehdi
Khosropour,Ahmad Reza
Ghozati,Kazem
author_role author
author2 Khosropour,Ahmad Reza
Ghozati,Kazem
author2_role author
author
dc.contributor.author.fl_str_mv Khodaei,Mohammad Mehdi
Khosropour,Ahmad Reza
Ghozati,Kazem
dc.subject.por.fl_str_mv beta-hydroxy thioethers
epoxides
disulfides
Bi(III) compounds
zinc
topic beta-hydroxy thioethers
epoxides
disulfides
Bi(III) compounds
zinc
description A new convenient method has been developed for the synthesis of beta-hydroxy thioethers with aryl disulfides and zinc powder in the presence of catalytic amounts of Bi(OTf)3 and Bi(TFA)3 in acetonitrile. The present method is very simple and the conditions tolerate a variety of acid-sensitive protecting groups. On the other hand, alkyl or benzyl disulfides afforded no corresponding thioethers under similar conditions. Then the observed regio- and chemoselectivity can be considered as a noteworthy advantage of this method.
publishDate 2005
dc.date.none.fl_str_mv 2005-06-01
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=S0103-50532005000400032
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532005000400032
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532005000400032
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.16 n.3b 2005
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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