Molybdenum‐Catalyzed Direct Synthesis of Pyrroles from Nitroarenes with Glycols as Reductants

A molybdenum-catalyzed synthesis of N-(hetero)aryl pyrroles directly from inexpensive and commonly available (hetero)nitroarenes via reduction with pinacol and annulation with 1,4-dicarbonyls or cyclobutane-1,2-diols has been described. The process does not require an inert atmosphere and tolerates...

Descripción completa

Detalles Bibliográficos
Autores: Gómez Gil, Sara, Suárez Pantiga, Samuel, Pedrosa Sáez, María de los Remedios, Sanz Díez, Roberto
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2024
País:España
Institución:Universidad de Burgos (UBU)
Repositorio:Repositorio Institucional de la Universidad de Burgos (RIUBU)
OAI Identifier:oai:riubu.ubu.es:10259/10505
Acceso en línea:http://hdl.handle.net/10259/10505
Access Level:acceso abierto
Palabra clave:Nitroarenes
Pyrroles
Reduction
Molybdenum
Glycols
Química
Química orgánica
Chemistry
Chemistry, Organic
id ES_0da72bea7c9dfd10ce4d01fcc1003359
oai_identifier_str oai:riubu.ubu.es:10259/10505
network_acronym_str ES
network_name_str España
repository_id_str
spelling Molybdenum‐Catalyzed Direct Synthesis of Pyrroles from Nitroarenes with Glycols as ReductantsGómez Gil, SaraSuárez Pantiga, SamuelPedrosa Sáez, María de los RemediosSanz Díez, RobertoNitroarenesPyrrolesReductionMolybdenumGlycolsQuímicaQuímica orgánicaChemistryChemistry, OrganicA molybdenum-catalyzed synthesis of N-(hetero)aryl pyrroles directly from inexpensive and commonly available (hetero)nitroarenes via reduction with pinacol and annulation with 1,4-dicarbonyls or cyclobutane-1,2-diols has been described. The process does not require an inert atmosphere and tolerates the presence of air and water. This non-noble catalytic system shows high chemoselectivity, allowing a diverse range of potentially reducible functional groups such as alkynes, alkenes, halogens, cyano, and carbonyls. Moreover, this strategy enables the reuse of a waste byproduct as reactant, facilitating the formation of challenging 1,4-dicarbonyls from accessible cyclobutane-1,2-diols used as reducing agents.We acknowledge the financial support from Ministerio de Ciencia, Innovación y Universidades (PID2020-115789GB-C21/AEI/10.1039/501100011033 and PDC2021-115789GB-C21), and Junta de Castilla y León and FEDER (BU028P23). S.G.-G. thanks Ministerio de Ciencia, Innovación y Universidades for a FPU predoctoral contract. S.S.-P. thanks Ministerio de Ciencia, Innovación y Universidades and “NextGenerationEU”/PRTR EU for a Ramón y Cajal contract (RYC2021-031533-I).Wiley202520252024info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10259/10505reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)instname:Universidad de Burgos (UBU)InglésAdvanced Synthesis & Catalysis. 2024, V. 367, n. 4, p. e202401170https://doi.org/10.1002/adsc.202401170Atribución-NoComercial 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc/4.0/info:eu-repo/semantics/openAccessoai:riubu.ubu.es:10259/105052026-05-28T07:56:11Z
dc.title.none.fl_str_mv Molybdenum‐Catalyzed Direct Synthesis of Pyrroles from Nitroarenes with Glycols as Reductants
title Molybdenum‐Catalyzed Direct Synthesis of Pyrroles from Nitroarenes with Glycols as Reductants
spellingShingle Molybdenum‐Catalyzed Direct Synthesis of Pyrroles from Nitroarenes with Glycols as Reductants
Gómez Gil, Sara
Nitroarenes
Pyrroles
Reduction
Molybdenum
Glycols
Química
Química orgánica
Chemistry
Chemistry, Organic
title_short Molybdenum‐Catalyzed Direct Synthesis of Pyrroles from Nitroarenes with Glycols as Reductants
title_full Molybdenum‐Catalyzed Direct Synthesis of Pyrroles from Nitroarenes with Glycols as Reductants
title_fullStr Molybdenum‐Catalyzed Direct Synthesis of Pyrroles from Nitroarenes with Glycols as Reductants
title_full_unstemmed Molybdenum‐Catalyzed Direct Synthesis of Pyrroles from Nitroarenes with Glycols as Reductants
title_sort Molybdenum‐Catalyzed Direct Synthesis of Pyrroles from Nitroarenes with Glycols as Reductants
dc.creator.none.fl_str_mv Gómez Gil, Sara
Suárez Pantiga, Samuel
Pedrosa Sáez, María de los Remedios
Sanz Díez, Roberto
author Gómez Gil, Sara
author_facet Gómez Gil, Sara
Suárez Pantiga, Samuel
Pedrosa Sáez, María de los Remedios
Sanz Díez, Roberto
author_role author
author2 Suárez Pantiga, Samuel
Pedrosa Sáez, María de los Remedios
Sanz Díez, Roberto
author2_role author
author
author
dc.subject.none.fl_str_mv Nitroarenes
Pyrroles
Reduction
Molybdenum
Glycols
Química
Química orgánica
Chemistry
Chemistry, Organic
topic Nitroarenes
Pyrroles
Reduction
Molybdenum
Glycols
Química
Química orgánica
Chemistry
Chemistry, Organic
description A molybdenum-catalyzed synthesis of N-(hetero)aryl pyrroles directly from inexpensive and commonly available (hetero)nitroarenes via reduction with pinacol and annulation with 1,4-dicarbonyls or cyclobutane-1,2-diols has been described. The process does not require an inert atmosphere and tolerates the presence of air and water. This non-noble catalytic system shows high chemoselectivity, allowing a diverse range of potentially reducible functional groups such as alkynes, alkenes, halogens, cyano, and carbonyls. Moreover, this strategy enables the reuse of a waste byproduct as reactant, facilitating the formation of challenging 1,4-dicarbonyls from accessible cyclobutane-1,2-diols used as reducing agents.
publishDate 2024
dc.date.none.fl_str_mv 2024
2025
2025
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10259/10505
url http://hdl.handle.net/10259/10505
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Advanced Synthesis & Catalysis. 2024, V. 367, n. 4, p. e202401170
https://doi.org/10.1002/adsc.202401170
dc.rights.none.fl_str_mv Atribución-NoComercial 4.0 Internacional
http://creativecommons.org/licenses/by-nc/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Atribución-NoComercial 4.0 Internacional
http://creativecommons.org/licenses/by-nc/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)
instname:Universidad de Burgos (UBU)
instname_str Universidad de Burgos (UBU)
reponame_str Repositorio Institucional de la Universidad de Burgos (RIUBU)
collection Repositorio Institucional de la Universidad de Burgos (RIUBU)
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869403351758667776
score 15.811543

Similares en LA Referencia