Metal- and Photocatalysis To Gain Regiocontrol and Stereodivergence in Hydroarylations of Unsymmetrical Dialkyl Alkynes

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dc.contributor.author Corpas, Javier
dc.contributor.author Quirós, M. Teresa
dc.contributor.author Mauleón, Pablo
dc.contributor.author Gómez Arrayás, Ramón
dc.contributor.author Carretero, Juan C.
dc.contributor.other UAM. Departamento de Química Orgánica es_ES
dc.date.accessioned 2019-11-05T11:38:12Z
dc.date.available 2019-11-05T11:38:12Z
dc.date.issued 2019-11-01
dc.identifier.citation ACS Catalysis 9.11 (2019):10567-10574 en_US
dc.identifier.issn 2155-5435 es_ES
dc.identifier.uri http://hdl.handle.net/10486/689111
dc.description This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://pubs.acs.org/doi/abs/10.1021/acscatal.9b02768 en_US
dc.description The Supporting Information (experimental procedures, spectral data, and complete DFT studies) is available (PDF) free of charge on the ACS Publications website at DOI: 10.1021/acscatal.9b02768. en_US
dc.description.abstract We report on a regioselective, stereodivergent catalytic hydroarylation of unsymmetrical dialkyl alkynes with arylboronic acids that allows highly selective access to either the E or Z diastereoisomer of trisubstituted alkenes. The E selectivity is achieved through syn-carbopalladation of the alkyne by Ar–Pd species followed by protodepalladation in which a 2-pyridyl sulfonyl (SO2Py) directing group enables complete control of the regioselectivity. Access to the complementary stereochemistry is achieved through a tandem Pd/Ir sequence, which includes hydroarylation and E→Z photoisomerization. Finally, facile removal of the directing group by reduction, Julia–Kocienski olefination, or Cu-catalyzed C(sp3)–C(sp2) or C(sp3)–C(sp3) cross coupling allows for the selective preparation of stereodefined olefins and dienes en_US
dc.description.sponsorship We thank the Spanish Ministerio de Economía, Industria y Competitividad and Fondo Europeo de Desarrollo Regional (Project: CTQ2015-66954-P, MINECO/FEDER, UE) and Ministerio de Ciencia, Innovación y Universidades (Agencia Estatal de Investigación)/FEDER (Project: PGC2018-098660−B-I00) for financial support. J.C. thanks the Ministerio de Educación, Cultura y Deporte (MECD), for a FPU fellowship. M.T.Q. thanks MINECO for a Juan de la Cierva Incorporación fellowship. The Centro de Computación Científica (UAM) is acknowledged for generous allocation of computer time en_US
dc.format.extent 29 pag. en_US
dc.format.mimetype application/pdf en
dc.language.iso eng en
dc.publisher American Chemical Society en_US
dc.relation.ispartof ACS Catalysis en_US
dc.rights © 2019 American Chemical Society en_US
dc.subject.other Alkyne hydroarylation en_US
dc.subject.other Regioselectivity en_US
dc.subject.other Stereodivergence en_US
dc.subject.other Tandem photo/metal catalysis en_US
dc.subject.other Removable directing group en_US
dc.subject.other Photocatalytic alkene isomerization en_US
dc.title Metal- and Photocatalysis To Gain Regiocontrol and Stereodivergence in Hydroarylations of Unsymmetrical Dialkyl Alkynes en_US
dc.type article en
dc.subject.eciencia Química es_ES
dc.date.embargoend 2020-11-01
dc.relation.publisherversion https://doi.org/10.1021/acscatal.9b02768 es_ES
dc.identifier.publicationfirstpage 10567 es_ES
dc.identifier.publicationissue 11 es_ES
dc.identifier.publicationlastpage 10574 es_ES
dc.identifier.publicationvolume 9 es_ES
dc.relation.projectID Gobierno de España. CTQ2015-66954-P es_ES
dc.relation.projectID Gobierno de España. PGC2018-098660−B-I00 es_ES
dc.type.version info:eu-repo/semantics/acceptedVersion en
dc.rights.accessRights embargoedAccess en
dc.authorUAM Corpas Pardo, Javier (281294)
dc.authorUAM Quirós López, María Teresa (278975)
dc.authorUAM Mauleón Pérez, Pablo (262860)
dc.authorUAM Gómez Arrayas, Ramón Jesús (260197)
dc.authorUAM Carretero Gonzálvez, Juan Carlos (260121)


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