Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes

Detalhes bibliográficos
Autor(a) principal: Siqueira,Fernanda A
Data de Publicação: 2011
Outros Autores: Ishikawa,Eloisa E, Fogaça,André, Faccio,Andréa T, Carneiro,Vânia M. T, Soares,Rafael R. S, Utaka,Aline, Tébéka,Iris R. M, Bielawski,Marcin, Olofsson,Berit, Silva Jr,Luiz F
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=S0103-50532011000900024
Resumo: A metal-free protocol was developed to synthesize indanes by ring contraction of 1, 2-dihydronaphthalenes promoted by PhI(OH)OTs (HTIB or Koser's reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2 , 2, 2-trifluoroethanol (TFE), 1 , 1, 1, 3, 3, 3-hexafluoroisopropanol (HFIP), and a 1:4 mixture of TFE:CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1, 3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry
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spelling Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenesindaneshypervalent iodinering contraction1 , 2-dihydronaphthalenesrearrangementsA metal-free protocol was developed to synthesize indanes by ring contraction of 1, 2-dihydronaphthalenes promoted by PhI(OH)OTs (HTIB or Koser's reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2 , 2, 2-trifluoroethanol (TFE), 1 , 1, 1, 3, 3, 3-hexafluoroisopropanol (HFIP), and a 1:4 mixture of TFE:CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1, 3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistrySociedade Brasileira de Química2011-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000900024Journal of the Brazilian Chemical Society v.22 n.9 2011reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532011000900024info:eu-repo/semantics/openAccessSiqueira,Fernanda AIshikawa,Eloisa EFogaça,AndréFaccio,Andréa TCarneiro,Vânia M. TSoares,Rafael R. SUtaka,AlineTébéka,Iris R. MBielawski,MarcinOlofsson,BeritSilva Jr,Luiz Feng2011-09-20T00:00:00Zoai:scielo:S0103-50532011000900024Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2011-09-20T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes
title Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes
spellingShingle Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes
Siqueira,Fernanda A
indanes
hypervalent iodine
ring contraction
1 , 2-dihydronaphthalenes
rearrangements
title_short Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes
title_full Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes
title_fullStr Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes
title_full_unstemmed Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes
title_sort Metal-free synthesis of indanes by iodine(III)-mediated ring contraction of 1, 2-dihydronaphthalenes
author Siqueira,Fernanda A
author_facet Siqueira,Fernanda A
Ishikawa,Eloisa E
Fogaça,André
Faccio,Andréa T
Carneiro,Vânia M. T
Soares,Rafael R. S
Utaka,Aline
Tébéka,Iris R. M
Bielawski,Marcin
Olofsson,Berit
Silva Jr,Luiz F
author_role author
author2 Ishikawa,Eloisa E
Fogaça,André
Faccio,Andréa T
Carneiro,Vânia M. T
Soares,Rafael R. S
Utaka,Aline
Tébéka,Iris R. M
Bielawski,Marcin
Olofsson,Berit
Silva Jr,Luiz F
author2_role author
author
author
author
author
author
author
author
author
author
dc.contributor.author.fl_str_mv Siqueira,Fernanda A
Ishikawa,Eloisa E
Fogaça,André
Faccio,Andréa T
Carneiro,Vânia M. T
Soares,Rafael R. S
Utaka,Aline
Tébéka,Iris R. M
Bielawski,Marcin
Olofsson,Berit
Silva Jr,Luiz F
dc.subject.por.fl_str_mv indanes
hypervalent iodine
ring contraction
1 , 2-dihydronaphthalenes
rearrangements
topic indanes
hypervalent iodine
ring contraction
1 , 2-dihydronaphthalenes
rearrangements
description A metal-free protocol was developed to synthesize indanes by ring contraction of 1, 2-dihydronaphthalenes promoted by PhI(OH)OTs (HTIB or Koser's reagent). This oxidative rearrangement can be performed in several solvents (MeOH, CH3CN, 2 , 2, 2-trifluoroethanol (TFE), 1 , 1, 1, 3, 3, 3-hexafluoroisopropanol (HFIP), and a 1:4 mixture of TFE:CH2Cl2) under mild conditions. The ring contraction diastereoselectively gives functionalized trans-1, 3-disubstituted indanes, which are difficult to obtain in synthetic organic chemistry
publishDate 2011
dc.date.none.fl_str_mv 2011-09-01
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=S0103-50532011000900024
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000900024
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532011000900024
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.22 n.9 2011
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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