Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzene

Detalhes bibliográficos
Autor(a) principal: Dawood,Kamal M.
Data de Publicação: 2014
Outros Autores: Hassaneen,Hamdi M., Abdelhadi,Hyam A., Ahmed,Mohamed S. M., Mohamed,Mohamed A.-M.
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=S0103-50532014000900020
Resumo: Sonogashira coupling of trimethylsilylacetylene with 4-alkyloxy-1-iodobenzenes gave 2-(4-(alkyloxy)phenyl)ethynyltrimethylsilanes which undergo deprotection via removal of TMS-group using tetrabutylammonium fluoride (TBAF) in THF at room temperature to afford the corresponding terminal 2-(4-(alkyloxy)phenyl)acetylenes. Regiocontrolled Sonogashira cross-coupling of 1,3,5-tribromobenzene with the terminal arylacetylenes in aqueous medium resulted in the formation of mono-, di- and tri-alkynylated benzene derivatives in moderate to good yields. Factors affecting the regioselective alkynylation were also examined.
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spelling Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzenearylacetylenescross-couplingcatalysispalladiumaqueous mediaSonogashira coupling of trimethylsilylacetylene with 4-alkyloxy-1-iodobenzenes gave 2-(4-(alkyloxy)phenyl)ethynyltrimethylsilanes which undergo deprotection via removal of TMS-group using tetrabutylammonium fluoride (TBAF) in THF at room temperature to afford the corresponding terminal 2-(4-(alkyloxy)phenyl)acetylenes. Regiocontrolled Sonogashira cross-coupling of 1,3,5-tribromobenzene with the terminal arylacetylenes in aqueous medium resulted in the formation of mono-, di- and tri-alkynylated benzene derivatives in moderate to good yields. Factors affecting the regioselective alkynylation were also examined.Sociedade Brasileira de Química2014-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014000900020Journal of the Brazilian Chemical Society v.25 n.9 2014reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.5935/0103-5053.20140163info:eu-repo/semantics/openAccessDawood,Kamal M.Hassaneen,Hamdi M.Abdelhadi,Hyam A.Ahmed,Mohamed S. M.Mohamed,Mohamed A.-M.eng2014-09-30T00:00:00Zoai:scielo:S0103-50532014000900020Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2014-09-30T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzene
title Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzene
spellingShingle Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzene
Dawood,Kamal M.
arylacetylenes
cross-coupling
catalysis
palladium
aqueous media
title_short Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzene
title_full Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzene
title_fullStr Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzene
title_full_unstemmed Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzene
title_sort Synthesis of unsymmetrical aryl-ethynylated benzenes via regiocontrolled Sonogashira reaction of 1,3,5-tribromobenzene
author Dawood,Kamal M.
author_facet Dawood,Kamal M.
Hassaneen,Hamdi M.
Abdelhadi,Hyam A.
Ahmed,Mohamed S. M.
Mohamed,Mohamed A.-M.
author_role author
author2 Hassaneen,Hamdi M.
Abdelhadi,Hyam A.
Ahmed,Mohamed S. M.
Mohamed,Mohamed A.-M.
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Dawood,Kamal M.
Hassaneen,Hamdi M.
Abdelhadi,Hyam A.
Ahmed,Mohamed S. M.
Mohamed,Mohamed A.-M.
dc.subject.por.fl_str_mv arylacetylenes
cross-coupling
catalysis
palladium
aqueous media
topic arylacetylenes
cross-coupling
catalysis
palladium
aqueous media
description Sonogashira coupling of trimethylsilylacetylene with 4-alkyloxy-1-iodobenzenes gave 2-(4-(alkyloxy)phenyl)ethynyltrimethylsilanes which undergo deprotection via removal of TMS-group using tetrabutylammonium fluoride (TBAF) in THF at room temperature to afford the corresponding terminal 2-(4-(alkyloxy)phenyl)acetylenes. Regiocontrolled Sonogashira cross-coupling of 1,3,5-tribromobenzene with the terminal arylacetylenes in aqueous medium resulted in the formation of mono-, di- and tri-alkynylated benzene derivatives in moderate to good yields. Factors affecting the regioselective alkynylation were also examined.
publishDate 2014
dc.date.none.fl_str_mv 2014-09-01
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=S0103-50532014000900020
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532014000900020
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.5935/0103-5053.20140163
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.25 n.9 2014
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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