dc.contributor.author | Legarda, Pablo D. | |
dc.contributor.author | García-Rubia, Alfonso | |
dc.contributor.author | Gómez Arrayas, Ramón Jesús | |
dc.contributor.author | Carretero Gonzálvez, Juan Carlos | |
dc.contributor.other | UAM. Departamento de Química Orgánica | es_ES |
dc.date.accessioned | 2016-04-15T08:54:55Z | |
dc.date.available | 2016-04-15T08:54:55Z | |
dc.date.issued | 2016-03-31 | |
dc.identifier.citation | Advanced Synthesis and Catalysis 358.7 (2016): 1065-1072 | en_US |
dc.identifier.issn | 1615-4150 (print) | es_ES |
dc.identifier.issn | 1615-4169 (online) | es_ES |
dc.identifier.uri | http://hdl.handle.net/10486/670656 | |
dc.description | This is the peer-reviewed version of the following article: Advanced Synthesis and Catalysis 358.7 (2016): 1065-1072, which has been published in final form at http://dx.doi.org/10.1002/adsc.201501129. This article may be used for non-commercial purposes in accordance with Wiley-VCH Terms and Conditions for Self-Archiving | en_US |
dc.description.abstract | A practical method for the palladium-cat-alyzed ortho-olefination of benzyl and phenethyl 2-pyridyl sulfones with electron-deficient alkenes using N-fluoro-2,4,6-trimethylpyridinium triflate ([F+]) as the terminal oxidant is described. The che-lating auxiliary (2-pyridyl)sulfonyl unit was demon-strated to be the key to the success of this reaction, which occurs efficiently with excellent regioselectiv-ity and monosubstitution selectivity. A variety of steric and electronic changes to both coupling part-ners is tolerated, including substitution at the ben-zylic position of the sulfone compound. Further-more, no appreciable loss of enantiopurity is ob-served when using non-racemic substrates. This method provides access to indane derivatives hold-ing three contiguous stereogenic centers with high diastereocontrol. The indane framework was con-structed by intramolecular Michael addition of the a-sulfonyl carbanion to the electrophilic alkene | en_US |
dc.description.sponsorship | We thank the Spanish Government (MINECO, CTQ2012- 35790) for financial support. P.D. L. thanks the Spanish Government (MINECO) for an FPU predoctoral fellowship | en_US |
dc.format.extent | 9 pag. | en |
dc.format.mimetype | application/pdf | en |
dc.language.iso | eng | en |
dc.publisher | Wiley-VCH Verlag | en_US |
dc.relation.ispartof | Advanced Synthesis and Catalysis | en_US |
dc.rights | © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim | en_US |
dc.subject.other | 2-pyridyl sulfones | en_US |
dc.subject.other | C-H alkenylation | en_US |
dc.subject.other | Indanes | en_US |
dc.subject.other | Michael-type addition | en_US |
dc.subject.other | Palladium | en_US |
dc.title | Palladium-Catalyzed Remote ortho-C-H Alkenylation of Alkyl Aryl Sulfones: Access to Densely Functionalized Indane Derivatives | en_US |
dc.type | article | en |
dc.subject.eciencia | Química | es_ES |
dc.date.embargoend | 2017-04-01 | |
dc.relation.publisherversion | http://dx.doi.org/10.1002/adsc.201501129 | es_ES |
dc.identifier.doi | 10.1002/adsc.201501129 | es_ES |
dc.identifier.publicationfirstpage | 1065 | es_ES |
dc.identifier.publicationissue | 7 | es_ES |
dc.identifier.publicationlastpage | 1072 | es_ES |
dc.identifier.publicationvolume | 358 | es_ES |
dc.relation.projectID | Gobierno de España. CTQ2012- 35790 | es_ES |
dc.type.version | info:eu-repo/semantics/acceptedVersion | en |
dc.rights.accessRights | openAccess | en |
dc.authorUAM | Carretero Gonzálvez, Juan Carlos (260121) | |
dc.authorUAM | Domingo Legarda, Pablo Miguel (264515) | |
dc.authorUAM | García Rubia, Alfonso (264385) | |
dc.authorUAM | Gómez Arrayas, Ramón Jesús (260197) | |
dc.facultadUAM | Facultad de Ciencias | |