Publicação
Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling
| Resumo: | The aim of this work is the synthesis of a formyl-arylthiophene derivative, using simple experimental techniques and commercially available reagents. The synthesis of this compound involves a palladium catalysed cross-coupling reaction (Suzuki-Miyaura coupling), between a boronic acid derivative and a heterocyclic brominated compound using DME as solvent and Na2CO3 as base. Different coupling components would be used in order to determine the influence of the structure of the boronic acid as well as the brominated compound on the yield of the Suzuki-Miyaura coupling reaction. Several experimental techniques will be considered such as heating at reflux under an inert atmosphere, liquid-liquid extraction, gravity and vacuum filtration, thin layer chromatography (TLC), column chromatography on silica gel and melting point. The determination of the structure of the compound synthesized will be also performed through 1H NMR and IR spectroscopic techniques. The duration of the experiment will be 3 sessions: session 1: preparation of 5-phenylthiophene-2-carbaldehyde; session 2: isolation of 5-phenylthiophene-2-carbaldehyde; session 3: purification of 5-phenylthiophene-2-carbaldehyde using column chromatography on silica gel. The difficulty level of this experiment is medium and the level of study is intermediate. |
|---|---|
| Autores principais: | Raposo, M. Manuela M. |
| Outros Autores: | Costa, Susana P. G.; Batista, Rosa Maria Ferreira; Ferreira, Rosa Cristina Moutinho |
| Assunto: | Chromatography NMR Suzuki-Miyaura cross-coupling Thiophene Boronic acid Aldehyde Synthesis Reactivity studies Organic Chemistry Experiments Laboratory Classroom Ciências Naturais::Ciências Químicas |
| Ano: | 2016 |
| País: | Portugal |
| Tipo de documento: | capítulo de livro |
| Tipo de acesso: | acesso restrito |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| _version_ | 1867438566365200384 |
|---|---|
| author | Raposo, M. Manuela M. |
| author2 | Costa, Susana P. G. Batista, Rosa Maria Ferreira Ferreira, Rosa Cristina Moutinho |
| author2_role | author author author |
| author_facet | Raposo, M. Manuela M. Costa, Susana P. G. Batista, Rosa Maria Ferreira Ferreira, Rosa Cristina Moutinho |
| author_role | author |
| contributor_name_str_mv | RepositóriUM - Universidade do Minho |
| country_str | PT |
| creators_json_txt | [{\"Person.name\":\"Raposo, M. Manuela M.\"},{\"Person.name\":\"Costa, Susana P. G.\"},{\"Person.name\":\"Batista, Rosa Maria Ferreira\"},{\"Person.name\":\"Ferreira, Rosa Cristina Moutinho\"}] |
| datacite.contributors.contributor.contributorName.fl_str_mv | RepositóriUM - Universidade do Minho |
| datacite.creators.creator.creatorName.fl_str_mv | Raposo, M. Manuela M. Costa, Susana P. G. Batista, Rosa Maria Ferreira Ferreira, Rosa Cristina Moutinho |
| datacite.date.Accepted.fl_str_mv | 2016-01-01T00:00:00Z |
| datacite.rights.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| datacite.subjects.subject.fl_str_mv | Chromatography NMR Suzuki-Miyaura cross-coupling Thiophene Boronic acid Aldehyde Synthesis Reactivity studies Organic Chemistry Experiments Laboratory Classroom Ciências Naturais::Ciências Químicas |
| datacite.titles.title.fl_str_mv | Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling |
| dc.contributor.none.fl_str_mv | RepositóriUM - Universidade do Minho |
| dc.creator.none.fl_str_mv | Raposo, M. Manuela M. Costa, Susana P. G. Batista, Rosa Maria Ferreira Ferreira, Rosa Cristina Moutinho |
| dc.date.Accepted.fl_str_mv | 2016-01-01T00:00:00Z |
| dc.format.none.fl_str_mv | application/pdf application/pdf |
| dc.identifier.none.fl_str_mv | https://hdl.handle.net/1822/49427 |
| dc.language.none.fl_str_mv | eng |
| dc.publisher.none.fl_str_mv | Royal Society of Chemistry |
| dc.rights.cclincense.fl_str_mv | http://creativecommons.org/licenses/by/4.0/ |
| dc.rights.none.fl_str_mv | http://purl.org/coar/access_right/c_16ec |
| dc.rights.rights.copyright.fl_str_mv | closedAccess |
| dc.subject.none.fl_str_mv | Chromatography NMR Suzuki-Miyaura cross-coupling Thiophene Boronic acid Aldehyde Synthesis Reactivity studies Organic Chemistry Experiments Laboratory Classroom Ciências Naturais::Ciências Químicas |
| dc.title.fl_str_mv | Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling |
| dc.type.none.fl_str_mv | http://purl.org/coar/resource_type/c_3248 |
| description | The aim of this work is the synthesis of a formyl-arylthiophene derivative, using simple experimental techniques and commercially available reagents. The synthesis of this compound involves a palladium catalysed cross-coupling reaction (Suzuki-Miyaura coupling), between a boronic acid derivative and a heterocyclic brominated compound using DME as solvent and Na2CO3 as base. Different coupling components would be used in order to determine the influence of the structure of the boronic acid as well as the brominated compound on the yield of the Suzuki-Miyaura coupling reaction. Several experimental techniques will be considered such as heating at reflux under an inert atmosphere, liquid-liquid extraction, gravity and vacuum filtration, thin layer chromatography (TLC), column chromatography on silica gel and melting point. The determination of the structure of the compound synthesized will be also performed through 1H NMR and IR spectroscopic techniques. The duration of the experiment will be 3 sessions: session 1: preparation of 5-phenylthiophene-2-carbaldehyde; session 2: isolation of 5-phenylthiophene-2-carbaldehyde; session 3: purification of 5-phenylthiophene-2-carbaldehyde using column chromatography on silica gel. The difficulty level of this experiment is medium and the level of study is intermediate. |
| dirty | 0 |
| eu_rights_str_mv | restrictedAccess |
| format | bookPart |
| fulltext.url.fl_str_mv | https://repositorium.uminho.pt/bitstreams/1f125392-7c9d-4d5d-a01d-94f5d5e83fc1/download |
| id | rum_d7ec00b6ff197a9496b4c7b072a2ca13 |
| identifier.url.fl_str_mv | https://hdl.handle.net/1822/49427 |
| instacron_str | repositorium |
| institution | Universidade do Minho |
| instname_str | Universidade do Minho |
| language | eng |
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| network_name_str | RepositóriUM - Universidade do Minho |
| oai_identifier_str | oai:repositorium.uminho.pt:1822/49427 |
| organization_str_mv | urn:organizationAcronym:repositorium |
| person_str_mv | Raposo, M. Manuela M. Costa, Susana P. G. Batista, Rosa Maria Ferreira Ferreira, Rosa Cristina Moutinho |
| publishDate | 2016 |
| publisher.none.fl_str_mv | Royal Society of Chemistry |
| reponame_str | RepositóriUM - Universidade do Minho |
| repository_id_str | urn:repositoryAcronym:rum |
| service_str_mv | urn:repositoryAcronym:rum |
| spelling | engRoyal Society of ChemistryporThe aim of this work is the synthesis of a formyl-arylthiophene derivative, using simple experimental techniques and commercially available reagents. The synthesis of this compound involves a palladium catalysed cross-coupling reaction (Suzuki-Miyaura coupling), between a boronic acid derivative and a heterocyclic brominated compound using DME as solvent and Na2CO3 as base. Different coupling components would be used in order to determine the influence of the structure of the boronic acid as well as the brominated compound on the yield of the Suzuki-Miyaura coupling reaction. Several experimental techniques will be considered such as heating at reflux under an inert atmosphere, liquid-liquid extraction, gravity and vacuum filtration, thin layer chromatography (TLC), column chromatography on silica gel and melting point. The determination of the structure of the compound synthesized will be also performed through 1H NMR and IR spectroscopic techniques. The duration of the experiment will be 3 sessions: session 1: preparation of 5-phenylthiophene-2-carbaldehyde; session 2: isolation of 5-phenylthiophene-2-carbaldehyde; session 3: purification of 5-phenylthiophene-2-carbaldehyde using column chromatography on silica gel. The difficulty level of this experiment is medium and the level of study is intermediate.application/pdfapplication/pdfporReactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura couplingRaposo, M. Manuela M.Costa, Susana P. G.Batista, Rosa Maria FerreiraFerreira, Rosa Cristina MoutinhoHostingInstitutionOrganizationalRepositóriUM - Universidade do Minhoe-mailmailto:repositorium@usdb.uminho.ptrepositorium@usdb.uminho.ptCITATIONRaposo, M. M. M.; Costa, S. P. G.: Batista, R. M. F.; Ferreira, R. C. M. in Comprehensive Organic Chemistry Experiments for the Laboratory Classroom (COCELC), “Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling”, Afonso, C. A. M.; Franzén, R.; Tan, B.; Candeias, N. R.; Simão, D.; Trindade, A.; Coelho, J. (Eds); Royal Society of Chemistry 2016, Chapter 142, Experiment 7.2., p 628-632 (ISBN 978-18-49739-63-4).ISBNIsPartOf978-18-49739-63-420162016-01-01T00:00:00ZHandlehttps://hdl.handle.net/1822/49427http://purl.org/coar/access_right/c_16ecrestricted accessChromatographyNMRSuzuki-Miyaura cross-couplingThiopheneBoronic acidAldehydeSynthesisReactivity studiesOrganic Chemistry ExperimentsLaboratory Classroomhttp://www.oecd.org/science/inno/38235147.pdfFields of Science and Technology (FOS)Ciências Naturais::Ciências Químicas254410 bytes399491 bytesliteraturehttp://purl.org/coar/resource_type/c_3248book part2016http://creativecommons.org/licenses/by/4.0/closedAccesshttp://purl.org/coar/access_right/c_16ecapplication/pdffulltexthttps://repositorium.uminho.pt/bitstreams/1f125392-7c9d-4d5d-a01d-94f5d5e83fc1/downloadhttp://purl.org/coar/access_right/c_16ecapplication/pdffulltexthttps://repositorium.uminho.pt/bitstreams/b818fcea-def0-4d22-8935-bef02de523cd/download |
| spellingShingle | Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling Raposo, M. Manuela M. Chromatography NMR Suzuki-Miyaura cross-coupling Thiophene Boronic acid Aldehyde Synthesis Reactivity studies Organic Chemistry Experiments Laboratory Classroom Ciências Naturais::Ciências Químicas |
| status | SINGLETON |
| subject.fl_str_mv | Chromatography NMR Suzuki-Miyaura cross-coupling Thiophene Boronic acid Aldehyde Synthesis Reactivity studies Organic Chemistry Experiments Laboratory Classroom |
| subject.other.fl_str_mv | Ciências Naturais::Ciências Químicas |
| title | Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling |
| title_full | Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling |
| title_fullStr | Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling |
| title_full_unstemmed | Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling |
| title_short | Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling |
| title_sort | Reactivity studies for the synthesis of 5-phenylthiophene-2-carbaldehyde by Suzuki-Miyaura coupling |
| topic | Chromatography NMR Suzuki-Miyaura cross-coupling Thiophene Boronic acid Aldehyde Synthesis Reactivity studies Organic Chemistry Experiments Laboratory Classroom Ciências Naturais::Ciências Químicas |
| topic_facet | Chromatography NMR Suzuki-Miyaura cross-coupling Thiophene Boronic acid Aldehyde Synthesis Reactivity studies Organic Chemistry Experiments Laboratory Classroom Ciências Naturais::Ciências Químicas |
| url | https://hdl.handle.net/1822/49427 |
| visible | 1 |