{ "dc.contributor.author": "Chen, Wei W." , "dc.contributor.author": "Cunillera, Anton" , "dc.contributor.author": "Chen, Dandan" , "dc.contributor.author": "Lethu, Sébastien" , "dc.contributor.author": "López de Moragas, Albert" , "dc.contributor.author": "Zhu, Jun" , "dc.contributor.author": "Solà i Puig, Miquel" , "dc.contributor.author": "Cuenca, Ana B." , "dc.contributor.author": "Shafir, Alexandr" , "dc.date.accessioned": "2020-11-26T09:10:47Z" , "dc.date.available": "2022-10-28T05:46:31Z" , "dc.date.issued": "2020-11-02" , "dc.identifier.issn": "1433-7851" , "dc.identifier.uri": "http://hdl.handle.net/10256/18693" , "dc.description.abstract": "A metal-free C-H allylation strategy is described to access diverse functionalized ortho-allyl-iodoarenes. The method employs hypervalent (diacetoxy)iodoarenes and proceeds through the iodane-guided 'iodonio-Claisen' allyl transfer. The use of allylsilanes bearing electron-withdrawing functional groups unlocks the functionalization of a broad range of substrates, including electron-neutral and electron-poor rings. The resulting ortho-allylated iodoarenes are versatile building blocks, with examples of downstream transformation including a concise synthesis of the experimental antimitotic core of Dosabulin. DFT calculations shed additional light on the reaction mechanism, with notable aspects including the virtually barrierless Si-to-I allyl transfer, and the aromatic character of the transition state structure for the [3,3] sigmatropic rearrangement" , "dc.description.sponsorship": "This work was funded by MINECO (CTQ2017-86936-P, CTQ2017-85341-P) and AGAUR (2017 SGR 01051, 2017 SGR 00294, 2017 SGR 00039). Financial support from CSIC, URL (2019-URL_Proj-034) and IQS-Obra Social La Caixa (2017-URLIntermac-010) is also gratefully acknowledged. The State Scholarship Fund (No. 201906310040, D.C.) from the China Scholarship Council (CSC), the National Science Foundation of China (21573179, J.Z.), the Top-Notch Young Talents Program of China (J.Z.) are also gratefully acknowledged" , "dc.format.extent": "7 p." , "dc.format.mimetype": "application/pdf" , "dc.language.iso": "eng" , "dc.publisher": "Wiley" , "dc.relation": "info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2017-85341-P/ES/AVANCES EN LA REACTIVIDAD DE FULLERENOS Y NANOTUBOS: ESTUDIOS TEORICO-EXPERIMENTALES DE CICLACIONES CATALIZADAS POR METALES DE TRANSICION/" , "dc.relation.isformatof": "Versió postprint del document publicat a: https://doi.org/10.1002/anie.202009369" , "dc.relation.ispartof": "© Angewandte Chemie International Edition, 2020, vol. 59, núm. 45, p. 20201-20207" , "dc.relation.ispartofseries": "Articles publicats (D-Q)" , "dc.rights": "Tots els drets reservats" , "dc.source": "Chen, Wei W. Cunillera, Anton Chen, Dandan Lethu, Sébastien López de Moragas, Albert Zhu, Jun Solà i Puig, Miquel Cuenca, Ana B. Shafir, Alexandr 2020 Iodane-guided ortho C-H allylation Angewandte Chemie International Edition 59 45 20201 20207" , "dc.subject": "Aromaticitat (Química)" , "dc.subject": "Aromaticity (Chemistry)" , "dc.subject": "Aromatic compounds" , "dc.subject": "Compostos aromàtics" , "dc.subject": "Hipervalència (química teòrica)" , "dc.subject": "Hypervalence (Theoretical chemistry)" , "dc.title": "Iodane-guided ortho C-H allylation" , "dc.type": "info:eu-repo/semantics/article" , "dc.rights.accessRights": "info:eu-repo/semantics/openAccess" , "dc.embargo.terms": "2021-11-02T00:00:00Z" , "dc.date.embargoEndDate": "info:eu-repo/date/embargoEnd/2021-11-02" , "dc.type.version": "info:eu-repo/semantics/acceptedVersion" , "dc.identifier.doi": "https://doi.org/10.1002/anie.202009369" , "dc.identifier.idgrec": "032184" , "dc.contributor.funder": "Ministerio de Economía y Competitividad (Espanya)" , "dc.type.peerreviewed": "peer-reviewed" , "dc.relation.FundingProgramme": "Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016" , "dc.relation.ProjectAcronym": "AVANCES EN LA REACTIVIDAD DE FULLERENOS Y NANOTUBOS: ESTUDIOS TEORICO-EXPERIMENTALES DE CICLACIONES CATALIZADAS POR METALES DE TRANSICION" , "dc.identifier.eissn": "1521-3773" }