Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans

Detalhes bibliográficos
Autor(a) principal: Rossini, Allan Felipe da Costa [UNIFESP]
Data de Publicação: 2014
Outros Autores: Frota, Carlise, Casagrande, Gleison Antonio, Pizzuti, Lucas, Raminelli, Cristiano [UNIFESP]
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNIFESP
Texto Completo: http://repositorio.unifesp.br/handle/11600/8653
http://dx.doi.org/10.5935/0103-5053.20140200
Resumo: A reação de acoplamento entre 2,6-diiodoanisóis e alcinos terminais usando Pd(PPh3)2Cl2 e CuI como catalisadores e diisopropilamina como base em tolueno a temperatura ambiente por 12 h produziu seletivamente 2-iodoanisóis aquinilados, em rendimentos de bons a excelentes (52-95%), os quais são blocos de construção úteis com potencial aplicação na síntese de benzo[b]furanos funcionalizados.
id UFSP_382aa25db3ce571a0abb276d25460ecd
oai_identifier_str oai:repositorio.unifesp.br:11600/8653
network_acronym_str UFSP
network_name_str Repositório Institucional da UNIFESP
repository_id_str 3465
spelling Rossini, Allan Felipe da Costa [UNIFESP]Frota, CarliseCasagrande, Gleison AntonioPizzuti, LucasRaminelli, Cristiano [UNIFESP]Universidade Federal de São Paulo (UNIFESP)Universidade Federal da Grande Dourados Faculdade de Ciências Exatas e Tecnologia2015-06-14T13:47:22Z2015-06-14T13:47:22Z2014-11-01Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 25, n. 11, p. 2125-2132, 2014.0103-50531678-4790http://repositorio.unifesp.br/handle/11600/8653http://dx.doi.org/10.5935/0103-5053.20140200S0103-50532014001100026.pdfS0103-5053201400110002610.5935/0103-5053.20140200WOS:000345241700026A reação de acoplamento entre 2,6-diiodoanisóis e alcinos terminais usando Pd(PPh3)2Cl2 e CuI como catalisadores e diisopropilamina como base em tolueno a temperatura ambiente por 12 h produziu seletivamente 2-iodoanisóis aquinilados, em rendimentos de bons a excelentes (52-95%), os quais são blocos de construção úteis com potencial aplicação na síntese de benzo[b]furanos funcionalizados.The coupling reaction between 2,6-diiodoanisoles and terminal alkynes using Pd(PPh3)2Cl2 and CuI as catalysts and diisopropylamine as base in toluene at room temperature for 12 h produced selectively alkynylated 2-iodoanisoles, in good to excellent yields (52-95%), which are useful building blocks with potential application in the synthesis of functionalized benzo[b]furans.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Fundacao de Apoio ao Desenvolvimento do EnsinoCiencia e Tecnologia do Estado de Mato Grosso do Sul (FUNDECT)Universidade Federal de São Paulo (UNIFESP) Departamento de Ciências Exatas e da TerraUniversidade Federal da Grande Dourados Faculdade de Ciências Exatas e TecnologiaUNIFESP, Depto. de Ciências Exatas e da TerraSciELO2125-2132engSociedade Brasileira de QuímicaJournal of the Brazilian Chemical SocietySonogashira reactionselective mono-couplingalkynylated anisolesdiiodinated benzo[b]furanspalladium and copper catalysisPalladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furansinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UNIFESPinstname:Universidade Federal de São Paulo (UNIFESP)instacron:UNIFESPORIGINALS0103-50532014001100026.pdfapplication/pdf337095${dspace.ui.url}/bitstream/11600/8653/1/S0103-50532014001100026.pdfce573950f50c99adf0524875009c5403MD51open accessTEXTS0103-50532014001100026.pdf.txtS0103-50532014001100026.pdf.txtExtracted texttext/plain29699${dspace.ui.url}/bitstream/11600/8653/9/S0103-50532014001100026.pdf.txtcb69b8cebf9118701210dbf2aeb104d5MD59open accessTHUMBNAILS0103-50532014001100026.pdf.jpgS0103-50532014001100026.pdf.jpgIM Thumbnailimage/jpeg6845${dspace.ui.url}/bitstream/11600/8653/11/S0103-50532014001100026.pdf.jpgfa7189faa7ab38b3aa79a3fb4d6ec017MD511open access11600/86532023-06-05 19:30:11.676open accessoai:repositorio.unifesp.br:11600/8653Repositório InstitucionalPUBhttp://www.repositorio.unifesp.br/oai/requestopendoar:34652023-06-05T22:30:11Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)false
dc.title.en.fl_str_mv Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans
title Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans
spellingShingle Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans
Rossini, Allan Felipe da Costa [UNIFESP]
Sonogashira reaction
selective mono-coupling
alkynylated anisoles
diiodinated benzo[b]furans
palladium and copper catalysis
title_short Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans
title_full Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans
title_fullStr Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans
title_full_unstemmed Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans
title_sort Palladium- and copper-catalyzed highly selective mono-coupling between 2,6-diiodoanisoles and terminal alkynes in the production of alkynylated anisoles as potential precursors of benzo[b]furans
author Rossini, Allan Felipe da Costa [UNIFESP]
author_facet Rossini, Allan Felipe da Costa [UNIFESP]
Frota, Carlise
Casagrande, Gleison Antonio
Pizzuti, Lucas
Raminelli, Cristiano [UNIFESP]
author_role author
author2 Frota, Carlise
Casagrande, Gleison Antonio
Pizzuti, Lucas
Raminelli, Cristiano [UNIFESP]
author2_role author
author
author
author
dc.contributor.institution.none.fl_str_mv Universidade Federal de São Paulo (UNIFESP)
Universidade Federal da Grande Dourados Faculdade de Ciências Exatas e Tecnologia
dc.contributor.author.fl_str_mv Rossini, Allan Felipe da Costa [UNIFESP]
Frota, Carlise
Casagrande, Gleison Antonio
Pizzuti, Lucas
Raminelli, Cristiano [UNIFESP]
dc.subject.eng.fl_str_mv Sonogashira reaction
selective mono-coupling
alkynylated anisoles
diiodinated benzo[b]furans
palladium and copper catalysis
topic Sonogashira reaction
selective mono-coupling
alkynylated anisoles
diiodinated benzo[b]furans
palladium and copper catalysis
description A reação de acoplamento entre 2,6-diiodoanisóis e alcinos terminais usando Pd(PPh3)2Cl2 e CuI como catalisadores e diisopropilamina como base em tolueno a temperatura ambiente por 12 h produziu seletivamente 2-iodoanisóis aquinilados, em rendimentos de bons a excelentes (52-95%), os quais são blocos de construção úteis com potencial aplicação na síntese de benzo[b]furanos funcionalizados.
publishDate 2014
dc.date.issued.fl_str_mv 2014-11-01
dc.date.accessioned.fl_str_mv 2015-06-14T13:47:22Z
dc.date.available.fl_str_mv 2015-06-14T13:47:22Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.citation.fl_str_mv Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 25, n. 11, p. 2125-2132, 2014.
dc.identifier.uri.fl_str_mv http://repositorio.unifesp.br/handle/11600/8653
http://dx.doi.org/10.5935/0103-5053.20140200
dc.identifier.issn.none.fl_str_mv 0103-5053
1678-4790
dc.identifier.file.none.fl_str_mv S0103-50532014001100026.pdf
dc.identifier.scielo.none.fl_str_mv S0103-50532014001100026
dc.identifier.doi.none.fl_str_mv 10.5935/0103-5053.20140200
dc.identifier.wos.none.fl_str_mv WOS:000345241700026
identifier_str_mv Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 25, n. 11, p. 2125-2132, 2014.
0103-5053
1678-4790
S0103-50532014001100026.pdf
S0103-50532014001100026
10.5935/0103-5053.20140200
WOS:000345241700026
url http://repositorio.unifesp.br/handle/11600/8653
http://dx.doi.org/10.5935/0103-5053.20140200
dc.language.iso.fl_str_mv eng
language eng
dc.relation.ispartof.none.fl_str_mv Journal of the Brazilian Chemical Society
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 2125-2132
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 reponame:Repositório Institucional da UNIFESP
instname:Universidade Federal de São Paulo (UNIFESP)
instacron:UNIFESP
instname_str Universidade Federal de São Paulo (UNIFESP)
instacron_str UNIFESP
institution UNIFESP
reponame_str Repositório Institucional da UNIFESP
collection Repositório Institucional da UNIFESP
bitstream.url.fl_str_mv ${dspace.ui.url}/bitstream/11600/8653/1/S0103-50532014001100026.pdf
${dspace.ui.url}/bitstream/11600/8653/9/S0103-50532014001100026.pdf.txt
${dspace.ui.url}/bitstream/11600/8653/11/S0103-50532014001100026.pdf.jpg
bitstream.checksum.fl_str_mv ce573950f50c99adf0524875009c5403
cb69b8cebf9118701210dbf2aeb104d5
fa7189faa7ab38b3aa79a3fb4d6ec017
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
repository.name.fl_str_mv Repositório Institucional da UNIFESP - Universidade Federal de São Paulo (UNIFESP)
repository.mail.fl_str_mv
_version_ 1783460341649244160

Registros relacionados