Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions.

Detalhes bibliográficos
Autor(a) principal: Castro, M.
Data de Publicação: 2016
Outros Autores: Castro, M. C. R., Raposo, M. Manuela M.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/44212
Resumo: A series of thienylpyrroles and bithienylpyrroles together with their formyl derivatives 5aed were synthesized using commercially or readily available coupling components, through three different palladium catalyzed cross-coupling reactions (Suzuki-Miyaura, Stille and decarboxylative coupling). The synthesis of compounds 5 via the Suzuki-Miyaura reaction produced the title compounds in better yields than the other coupling reactions, while, decarboxylative coupling resulted in the lower yields. UV-visible and 1H NMR studies confirm the existence of significant intramolecular charge transfer (ICT) from the donor pyrrole heterocycle to the acceptor group and a high polarizability of the whole pi-conjugated systems. Together these characteristics indicate their strong potential as versatile precursors for the preparation of push-pull heterocyclic compounds for optical applications.
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spelling Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions.pi-Conjugated systemsFormyl-substituted (bi)thienylpyrrolesThiophenePyrroleSuzuki-Miyaura couplingStille couplingDecarboxylative couplingUV-vis spectroscopyNonlinear optical (NLO) precursorsStifle couplingp-Conjugated systemsCiências Naturais::Ciências QuímicasScience & TechnologyA series of thienylpyrroles and bithienylpyrroles together with their formyl derivatives 5aed were synthesized using commercially or readily available coupling components, through three different palladium catalyzed cross-coupling reactions (Suzuki-Miyaura, Stille and decarboxylative coupling). The synthesis of compounds 5 via the Suzuki-Miyaura reaction produced the title compounds in better yields than the other coupling reactions, while, decarboxylative coupling resulted in the lower yields. UV-visible and 1H NMR studies confirm the existence of significant intramolecular charge transfer (ICT) from the donor pyrrole heterocycle to the acceptor group and a high polarizability of the whole pi-conjugated systems. Together these characteristics indicate their strong potential as versatile precursors for the preparation of push-pull heterocyclic compounds for optical applications.The authors thank the Fundação para a Ciência e Tecnologia (Portugal) and FEDER-COMPETE for financial support through the Centro de Química – Universidade do Minho, Projects PTDC/QUI/66251/2006 (FCOMP-01-0124-FEDER-007429), CQ/UM PEst-C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-037302) and a PhD grant to M. C. R. Castro (SFRH/BD/78037/2011). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, with funds from FCT.ElsevierUniversidade do MinhoCastro, M.Castro, M. C. R.Raposo, M. Manuela M.20162016-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/44212engCidalia, M., Castro, R., Manuela, M., & Raposo, M. (2016). Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions. Tetrahedron, 72(15), 1881-1887. doi: 10.1016/j.tet.2016.02.0540040-402010.1016/j.tet.2016.02.054http://dx.doi.org/10.1016/j.tet.2016.02.054info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-05-11T05:14:06Zoai:repositorium.sdum.uminho.pt:1822/44212Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-05-11T05:14:06Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions.
title Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions.
spellingShingle Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions.
Castro, M.
pi-Conjugated systems
Formyl-substituted (bi)thienylpyrroles
Thiophene
Pyrrole
Suzuki-Miyaura coupling
Stille coupling
Decarboxylative coupling
UV-vis spectroscopy
Nonlinear optical (NLO) precursors
Stifle coupling
p-Conjugated systems
Ciências Naturais::Ciências Químicas
Science & Technology
title_short Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions.
title_full Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions.
title_fullStr Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions.
title_full_unstemmed Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions.
title_sort Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions.
author Castro, M.
author_facet Castro, M.
Castro, M. C. R.
Raposo, M. Manuela M.
author_role author
author2 Castro, M. C. R.
Raposo, M. Manuela M.
author2_role author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Castro, M.
Castro, M. C. R.
Raposo, M. Manuela M.
dc.subject.por.fl_str_mv pi-Conjugated systems
Formyl-substituted (bi)thienylpyrroles
Thiophene
Pyrrole
Suzuki-Miyaura coupling
Stille coupling
Decarboxylative coupling
UV-vis spectroscopy
Nonlinear optical (NLO) precursors
Stifle coupling
p-Conjugated systems
Ciências Naturais::Ciências Químicas
Science & Technology
topic pi-Conjugated systems
Formyl-substituted (bi)thienylpyrroles
Thiophene
Pyrrole
Suzuki-Miyaura coupling
Stille coupling
Decarboxylative coupling
UV-vis spectroscopy
Nonlinear optical (NLO) precursors
Stifle coupling
p-Conjugated systems
Ciências Naturais::Ciências Químicas
Science & Technology
description A series of thienylpyrroles and bithienylpyrroles together with their formyl derivatives 5aed were synthesized using commercially or readily available coupling components, through three different palladium catalyzed cross-coupling reactions (Suzuki-Miyaura, Stille and decarboxylative coupling). The synthesis of compounds 5 via the Suzuki-Miyaura reaction produced the title compounds in better yields than the other coupling reactions, while, decarboxylative coupling resulted in the lower yields. UV-visible and 1H NMR studies confirm the existence of significant intramolecular charge transfer (ICT) from the donor pyrrole heterocycle to the acceptor group and a high polarizability of the whole pi-conjugated systems. Together these characteristics indicate their strong potential as versatile precursors for the preparation of push-pull heterocyclic compounds for optical applications.
publishDate 2016
dc.date.none.fl_str_mv 2016
2016-01-01T00:00:00Z
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.uri.fl_str_mv http://hdl.handle.net/1822/44212
url http://hdl.handle.net/1822/44212
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Cidalia, M., Castro, R., Manuela, M., & Raposo, M. (2016). Synthesis of pi-conjugated systems bearing thiophene and pyrrole heterocycles through palladium catalyzed cross-coupling reactions. Tetrahedron, 72(15), 1881-1887. doi: 10.1016/j.tet.2016.02.054
0040-4020
10.1016/j.tet.2016.02.054
http://dx.doi.org/10.1016/j.tet.2016.02.054
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv mluisa.alvim@gmail.com
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