Mostrar o rexistro simple do ítem
Indium(III)-Catalyzed Stereoselective Synthesis of Tricyclic Frameworks by Cascade Cycloisomerization Reactions of Aryl 1,5-Enynes
dc.contributor.author | Millán, Ramón | |
dc.contributor.author | Rodríguez, Jaime | |
dc.contributor.author | Sarandeses, Luis A. | |
dc.contributor.author | Gómez Bengoa, Enrique | |
dc.contributor.author | Pérez Sestelo, José | |
dc.date.accessioned | 2021-10-29T12:54:33Z | |
dc.date.available | 2021-10-29T12:54:33Z | |
dc.date.issued | 2021-06-25 | |
dc.identifier.citation | Millán, R. E.; Rodríguez, J.; Sarandeses, L. A.; Gómez-Bengoa, E.; Sestelo, J. P. J. Org. Chem. 2021, 86, 9515. https://doi.org/10.1021/acs.joc.1c00825 | es_ES |
dc.identifier.issn | 0022-3263 | |
dc.identifier.issn | 1520-6904 | |
dc.identifier.uri | http://hdl.handle.net/2183/28771 | |
dc.description | Financiado para publicación en acceso aberto: Universidade da Coruña/CISUG | |
dc.description | The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.joc.1c00825 (https://pubs.acs.org/doi/suppl/10.1021/acs.joc.1c00825/suppl_file/jo1c00825_si_001.pdf) | |
dc.description.abstract | [Abstract] The indium(III)-catalyzed cascade cycloisomerization reaction of 1,5-enynes with pendant aryl nucleophiles is reported. The reaction proceeds in cascade under mild reaction conditions, using InI₃ (5 mol %) as a catalyst with a range of 1,5-enynes furnished with aryl groups (phenyl and phenol) at alkene (E and Z isomers) and with terminal and internal alkynes. Using 1-bromo-1,5-enynes, a one-pot sequential indium-catalyzed cycloisomerization and palladium-catalyzed cross-coupling with triorganoindium reagents were developed. The double cyclization is stereospecific and operates via a biomimetic cascade cation-olefin through 1,5-enyne cyclization (6-endo-dig) and subsequent C–C hydroarylation or C–O phenoxycyclization. Density functional theory (DFT) computational studies on 1,5-enynyl aryl ethers support a two-step mechanism where the first stereoselective 1,5-enyne cyclization produces a nonclassical carbocation intermediate that evolves to the tricyclic reaction product through a SᴇAr mechanism. Using this approach, a variety of tricyclic heterocycles such as benzo[b]chromenes, phenanthridines, xanthenes, and spiroheterocyclic compounds are efficiently synthesized with high atom economy. | es_ES |
dc.description.sponsorship | We thank the Spanish Ministerio de Ciencia, Innovación y Universidades (PGC2018-097792-B-I00 and PID 2019-110008GB-I00), Xunta de Galicia (GRC2018/039), IZO-SGI SGIker of UPV/EHU, and EDRF funds for financial and human support | es_ES |
dc.description.sponsorship | Xunta de Galicia; GRC2018/039 | es_ES |
dc.description.uri | https://pubs.acs.org/doi/suppl/10.1021/acs.joc.1c00825/suppl_file/jo1c00825_si_001.pdf | |
dc.language.iso | eng | es_ES |
dc.publisher | American Chemical Society | es_ES |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PGC2018-097792-B-I00/ES/EL INDIO COMO HERRAMIENTA SINTETICA EN REACCIONES DE ACOPLAMIENTO Y EN CATALISIS | |
dc.relation | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-110008GB-I00/ES/ESTUDIOS COMPUTACIONALES Y EXPERIMENTALES SOBRE ACTIVACION C-H CATALIZADA POR PALADIO | |
dc.relation.uri | https://doi.org/10.1021/acs.joc.1c00825 | es_ES |
dc.rights | Atribución 4.0 Internacional | es_ES |
dc.rights.uri | http://creativecommons.org/licenses/by/4.0/ | * |
dc.title | Indium(III)-Catalyzed Stereoselective Synthesis of Tricyclic Frameworks by Cascade Cycloisomerization Reactions of Aryl 1,5-Enynes | es_ES |
dc.type | info:eu-repo/semantics/article | es_ES |
dc.rights.access | info:eu-repo/semantics/openAccess | es_ES |
UDC.journalTitle | The Journal of Organic Chemistry | es_ES |
UDC.volume | 86 | es_ES |
UDC.issue | 14 | es_ES |
UDC.startPage | 9515 | es_ES |
UDC.endPage | 9529 | es_ES |