Transition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles

Simple item page
dc.contributor.authorAlmendros Requena, Pedro
dc.contributor.authorYanai, Hikaru
dc.contributor.authorHoshikawa, Shoki
dc.contributor.authorAragoncillo Abanades, Cristina
dc.contributor.authorLázaro Milla, Carlos
dc.contributor.authorToledano-Pinedo, Mireia
dc.contributor.authorMatsumoto, Takashi
dc.contributor.authorAlcaide Alañón, Benito
dc.date.accessioned2024-01-09T09:50:34Z
dc.date.available2024-01-09T09:50:34Z
dc.date.issued2018
dc.description.abstractSeveral heterocycles reacted with shelf-stable 2-(2-fluoropyridinium-1-yl)-1,1-bis[(trifluoromethyl)sulfonyl] ethan-1-ide, a latent Tf2CvCH2 source, to give rise in a mild and controllable way to adducts via direct C–H bis[(trifluoromethyl)sulfonyl]ethylation reactions. This metal- and irradiation-free protocol is convenient. Besides, the volatile side-product 2 fluoropyridine can be smoothly eliminated under vacuum, which facilitates purification. The substrate scope survey discloses that exquisite chemo- and regioselectivities are achieved in a variety of heterocyclic systems. Of particular interest are the late-stage structural modification of known pharmaceuticals, such as the marketed drugs Phenazone (Antipyrine) and Edaravone, and the development of a water soluble fluorescent dye.
dc.description.departmentDepto. de Química Orgánica
dc.description.facultyFac. de Ciencias Químicas
dc.description.refereedTRUE
dc.description.sponsorshipMinisterio de Economía, Comercio y Empresa (España)
dc.description.sponsorshipEuropean Commission
dc.description.statuspub
dc.identifier.citationAlmendros P, Yanai H, Hoshikawa S, Aragoncillo C, Lázaro-Milla C, Toledano-Pinedo M, Matsumoto T, Alcaide B. Transition Metal-Free Controlled Synthesis of Bis[(Trifluoromethyl)Sulfonyl] Ethyl-Decorated Heterocycles. Org. Chem. Front. 2018, 5, 3163-3169.
dc.identifier.doi10.1039/c8qo00955d
dc.identifier.issn2052-4129
dc.identifier.officialurlhttps://doi.org/10.1039/c8qo00955d
dc.identifier.urihttps://hdl.handle.net/20.500.14352/91958
dc.journal.titleOrganic Chemistry Frontiers
dc.language.isoeng
dc.page.final3169
dc.page.initial3163
dc.publisherRoyal Society of Chemistry
dc.relation.projectID(Projects CTQ2015-65060-C2-1-P and CTQ2015-65060- C2-2-P)
dc.rights.accessRightsmetadata only access
dc.subject.cdu547
dc.subject.keywordHeterocycles
dc.subject.keywordTriflyl group
dc.subject.ucmCiencias
dc.subject.ucmQuímica orgánica (Química)
dc.subject.unesco2306.10 Compuestos Heterocíclicos
dc.titleTransition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles
dc.typejournal article
dc.type.hasVersionVoR
dc.volume.number5
dspace.entity.typePublication
relation.isAuthorOfPublicationee8363b4-4019-453d-abd3-6258ecc4299f
relation.isAuthorOfPublication8b257537-0758-463d-9e75-ac1e3d55f9a6
relation.isAuthorOfPublication6ddf42bc-c237-4feb-bc28-f9c7484ed291
relation.isAuthorOfPublicationdbc0191b-3484-4873-8c9c-d93ee68928be
relation.isAuthorOfPublication.latestForDiscoverydbc0191b-3484-4873-8c9c-d93ee68928be
Download
Collections
Artículos