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dc.contributor.author | Mingueza-Verdejo, Paloma | es_ES |
dc.contributor.author | Rodríguez-Nuévalos, Silvia | es_ES |
dc.contributor.author | Oliver-Meseguer, Judit | es_ES |
dc.contributor.author | Leyva Perez, Antonio | es_ES |
dc.date.accessioned | 2024-10-07T18:07:46Z | |
dc.date.available | 2024-10-07T18:07:46Z | |
dc.date.issued | 2024-07-02 | es_ES |
dc.identifier.issn | 0947-6539 | es_ES |
dc.identifier.uri | http://hdl.handle.net/10251/209466 | |
dc.description.abstract | [EN] 2,5-Dimethyl-2,4-hexadiene is a readily available and easily managable compound, whose symmetric and polymethylated dienic structure should be prone to engage in cross-metathesis reactions with other alkenes, but this has not been apparently exploited so far. Here we show that this reactant enables the easy synthesis of tri- and tetra-susbtituted alkenes (i. e. isobutylenyl and prenyl groups) from simple alkenes under mild reaction conditions, not only with the conventional 2nd generation Grubbs catalyst but also with other Grela-type catalyts such as StickyCat,TM AquaMetTM and GreenCatTM. The use of liquid and low volatile 2,5-dimethyl-2,4-hexadiene avoids the use of gaseous alkene reactants and, besides, showcases the reactivity of polyisoprene (rubber), thus allowing to optimize the reaction conditions for rubber upcycling, after metathesis reaction of the pristine or used polymer with simple alkenes. These results bring low volatile isoprene-type compounds as privileged poly-substituted reactants for alkene cross-metathesis reactions.; 2,5-Dimethyl-2,4-hexadiene is presented here as a suitable and selective reactant for delivering either prenyl or isobutylenyl groups to alkenes through a cross-metathesis reaction. The process smoothly operates at room temperature, give high yields of products, includes a late-stage transformation, and enables the valorization of real samples of recycled rubber. image | es_ES |
dc.description.sponsorship | This work is part of the project PID2020-115100GB-I00 funded by MCIN/AEI/10.13039/501100011033MICIIN (Spain). Financial support by Severo Ochoa centre of excellence program (CEX2021-001230-S) is gratefully acknowledged. The work has also been funded by Generalitat Valenciana (INNEST/2022/20 from Agencia Valenciana de la Innovacio). P.M.-V. thanks ITQ, UPV-CSIC for concession of a contract (PAID 01-20). S.R.-N. thanks Agencia Valenciana de la Innovacio for a contract (INNEST/2022/20). J.O.-M. thanks the MICIIN for the concession of the Ramon y Cajal contract RYC2022-036154-I (funded by MCIN/AEI/10.13039/501100011033). | es_ES |
dc.language | Inglés | es_ES |
dc.publisher | John Wiley & Sons | es_ES |
dc.relation.ispartof | Chemistry - A European Journal | es_ES |
dc.rights | Reconocimiento - No comercial - Sin obra derivada (by-nc-nd) | es_ES |
dc.subject | Alkene cross-metathesis | es_ES |
dc.subject | 2,5-Dimethyl-2,4-hexadiene | es_ES |
dc.subject | Rubber valorization | es_ES |
dc.subject | Prenylation | es_ES |
dc.subject | Isobutenyl | es_ES |
dc.title | Alkene Cross-Metathesis with 2,5-Dimethyl-2,4-Hexadiene Enables Isobutylenyl/Prenyl Functionalizations and Rubber Valorization | es_ES |
dc.type | Artículo | es_ES |
dc.identifier.doi | 10.1002/chem.202400860 | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-115100GB-I00/ES/CLUSTERES CATALITICOS MULTIMETALICOS Y DE ALTA ENTROPIA PARA SINTESIS ORGANICA/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/ITQ//PAID 01-20/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/AVI//INNEST%2F2022%2F20/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/MICINN//CEX2021-001230-S/ | es_ES |
dc.relation.projectID | info:eu-repo/grantAgreement/MICINN//RyC2022-036154-I/ | es_ES |
dc.rights.accessRights | Abierto | es_ES |
dc.contributor.affiliation | Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química | es_ES |
dc.description.bibliographicCitation | Mingueza-Verdejo, P.; Rodríguez-Nuévalos, S.; Oliver-Meseguer, J.; Leyva Perez, A. (2024). Alkene Cross-Metathesis with 2,5-Dimethyl-2,4-Hexadiene Enables Isobutylenyl/Prenyl Functionalizations and Rubber Valorization. Chemistry - A European Journal. https://doi.org/10.1002/chem.202400860 | es_ES |
dc.description.accrualMethod | S | es_ES |
dc.relation.publisherversion | https://doi.org/10.1002/chem.202400860 | es_ES |
dc.type.version | info:eu-repo/semantics/publishedVersion | es_ES |
dc.identifier.pmid | 38699858 | es_ES |
dc.relation.pasarela | S\526447 | es_ES |
dc.contributor.funder | Agencia Estatal de Investigación | es_ES |
dc.contributor.funder | Ministerio de Ciencia e Innovación | es_ES |
dc.contributor.funder | Agència Valenciana de la Innovació | es_ES |
dc.contributor.funder | Instituto de Tecnología Química UPV-CSIC | es_ES |