Selective synthesis of phenanthrenes and dihydrophenanthrenes via gold-catalyzed cycloisomerization of biphenyl embedded trienynes

Readily available o′-alkenyl-o-alkynylbiaryls, a particular type of 1,7-enynes, undergo a selective cycloisomerization reaction in the presence of a gold(I) catalyst to give interesting phenanthrene and dihydrophenanthrene derivatives in high yields. The solvent used provokes a switch in the evoluti...

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Detalles Bibliográficos
Autores: Milián, Ana, García García, Patricia, Pérez Redondo, Adrián, Sanz Díez, Roberto, Vaquero, Juan J., Fernández Rodríguez, Manuel A.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Institución:Universidad de Burgos (UBU)
Repositorio:Repositorio Institucional de la Universidad de Burgos (RIUBU)
OAI Identifier:oai:riubu.ubu.es:10259/5546
Acceso en línea:http://hdl.handle.net/10259/5546
Access Level:acceso abierto
Palabra clave:Hydrocarbons
Catalysts
Isomerization
Aromatic compounds
Solvents
Química orgánica
Chemistry, Organic
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spelling Selective synthesis of phenanthrenes and dihydrophenanthrenes via gold-catalyzed cycloisomerization of biphenyl embedded trienynesMilián, AnaGarcía García, PatriciaPérez Redondo, AdriánSanz Díez, RobertoVaquero, Juan J.Fernández Rodríguez, Manuel A.HydrocarbonsCatalystsIsomerizationAromatic compoundsSolventsQuímica orgánicaChemistry, OrganicReadily available o′-alkenyl-o-alkynylbiaryls, a particular type of 1,7-enynes, undergo a selective cycloisomerization reaction in the presence of a gold(I) catalyst to give interesting phenanthrene and dihydrophenanthrene derivatives in high yields. The solvent used provokes a switch in the evolution of the gold intermediate and plays a key role in the reaction outcome.Ministerio de Economıá y Competitividad (MINECO), AEI and FEDER (projects CTQ2017- 85263-R and CTQ2016-75023-C2-1-P), Instituto de Salud Carlos III (FEDER funds, ISCIII RETIC REDINREN RD16/ 0009/0015), Junta de Castilla y León and FEDER (BU291P18), and University of Alcalá (projects CCGP2017- EXP/016 and CCG2018/EXP-008American Chemical Society202020202020info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttp://hdl.handle.net/10259/5546reponame:Repositorio Institucional de la Universidad de Burgos (RIUBU)instname:Universidad de Burgos (UBU)InglésOrganic Letters. 2020, V. 22, n. 21, p. 8464–8469https://doi.org/10.1021/acs.orglett.0c03067info:eu-repo/grantAgreement/MINECO/CTQ2017- 85263-R/info:eu-repo/grantAgreement/MINECO/CTQ2016-75023-C2-1-P/info:eu-repo/grantAgreement/JCyL/BU291P18/info:eu-repo/grantAgreement/Instituto de Salud Carlos III/RD16/ 0009info:eu-repo/grantAgreement/UAH/CCGP2017- EXP/016info:eu-repo/grantAgreement/UAH/CCG2018/EXP-008info:eu-repo/semantics/openAccessoai:riubu.ubu.es:10259/55462026-05-28T07:56:11Z
dc.title.none.fl_str_mv Selective synthesis of phenanthrenes and dihydrophenanthrenes via gold-catalyzed cycloisomerization of biphenyl embedded trienynes
title Selective synthesis of phenanthrenes and dihydrophenanthrenes via gold-catalyzed cycloisomerization of biphenyl embedded trienynes
spellingShingle Selective synthesis of phenanthrenes and dihydrophenanthrenes via gold-catalyzed cycloisomerization of biphenyl embedded trienynes
Milián, Ana
Hydrocarbons
Catalysts
Isomerization
Aromatic compounds
Solvents
Química orgánica
Chemistry, Organic
title_short Selective synthesis of phenanthrenes and dihydrophenanthrenes via gold-catalyzed cycloisomerization of biphenyl embedded trienynes
title_full Selective synthesis of phenanthrenes and dihydrophenanthrenes via gold-catalyzed cycloisomerization of biphenyl embedded trienynes
title_fullStr Selective synthesis of phenanthrenes and dihydrophenanthrenes via gold-catalyzed cycloisomerization of biphenyl embedded trienynes
title_full_unstemmed Selective synthesis of phenanthrenes and dihydrophenanthrenes via gold-catalyzed cycloisomerization of biphenyl embedded trienynes
title_sort Selective synthesis of phenanthrenes and dihydrophenanthrenes via gold-catalyzed cycloisomerization of biphenyl embedded trienynes
dc.creator.none.fl_str_mv Milián, Ana
García García, Patricia
Pérez Redondo, Adrián
Sanz Díez, Roberto
Vaquero, Juan J.
Fernández Rodríguez, Manuel A.
author Milián, Ana
author_facet Milián, Ana
García García, Patricia
Pérez Redondo, Adrián
Sanz Díez, Roberto
Vaquero, Juan J.
Fernández Rodríguez, Manuel A.
author_role author
author2 García García, Patricia
Pérez Redondo, Adrián
Sanz Díez, Roberto
Vaquero, Juan J.
Fernández Rodríguez, Manuel A.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Hydrocarbons
Catalysts
Isomerization
Aromatic compounds
Solvents
Química orgánica
Chemistry, Organic
topic Hydrocarbons
Catalysts
Isomerization
Aromatic compounds
Solvents
Química orgánica
Chemistry, Organic
description Readily available o′-alkenyl-o-alkynylbiaryls, a particular type of 1,7-enynes, undergo a selective cycloisomerization reaction in the presence of a gold(I) catalyst to give interesting phenanthrene and dihydrophenanthrene derivatives in high yields. The solvent used provokes a switch in the evolution of the gold intermediate and plays a key role in the reaction outcome.
publishDate 2020
dc.date.none.fl_str_mv 2020
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10259/5546
url http://hdl.handle.net/10259/5546
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Organic Letters. 2020, V. 22, n. 21, p. 8464–8469
https://doi.org/10.1021/acs.orglett.0c03067
info:eu-repo/grantAgreement/MINECO/CTQ2017- 85263-R/
info:eu-repo/grantAgreement/MINECO/CTQ2016-75023-C2-1-P/
info:eu-repo/grantAgreement/JCyL/BU291P18/
info:eu-repo/grantAgreement/Instituto de Salud Carlos III/RD16/ 0009
info:eu-repo/grantAgreement/UAH/CCGP2017- EXP/016
info:eu-repo/grantAgreement/UAH/CCG2018/EXP-008
dc.rights.none.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 American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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
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score 15,30478

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