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5-(Cyano)dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and Cyanocyclizations

dc.contributor.authorLi, Xiangdong
dc.contributor.authorGolz, Christopher
dc.contributor.authorAlcarazo, Manuel
dc.date.accessioned2019-09-30T10:41:00Z
dc.date.available2019-09-30T10:41:00Z
dc.date.issued2019de
dc.relation.ISSN1521-3773de
dc.identifier.urihttp://resolver.sub.uni-goettingen.de/purl?gs-1/16427
dc.description.abstractThe synthesis of 5-(cyano)dibenzothiophenium triflate 9, prepared by activation of dibenzo[b,d]thiophene-5-oxide with Tf2 O and subsequent reaction with TMSCN is reported, and its reactivity as electrophilic cyanation reagent evaluated. The scalable preparation, easy handling and broad substrate scope of the electrophilic cyanation promoted by 9, which includes amines, thiols, silyl enol ethers, alkenes, electron rich (hetero)arenes and polyaromatic hydrocarbons, illustrate the synthetic potential of this reagent. Importantly, Lewis acid activation of the reagent is not required for the transfer process. We additionally report herein biomimetic cyanocyclization cascade reactions, which are not promoted by typical electrophilic cyanation reagents, demonstrating the superior ability of 9 to trigger challenging transformations.de
dc.language.isoengde
dc.rightsopenAccess
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectelectrophilic cyanation; metal-free functionalizations; sulfonium salts; transfer reagents; umpolungde
dc.subject.ddc540
dc.title5-(Cyano)dibenzothiophenium Triflate: A Sulfur-Based Reagent for Electrophilic Cyanation and Cyanocyclizationsde
dc.typejournalArticlede
dc.identifier.doi10.1002/anie.201904557
dc.type.versionpublishedVersionde
dc.bibliographicCitation.volume58de
dc.bibliographicCitation.issue28de
dc.bibliographicCitation.firstPage9496de
dc.bibliographicCitation.lastPage9500de
dc.type.subtypejournalArticle
dc.identifier.pmid31091342
dc.description.statuspeerReviewedde
dc.bibliographicCitation.journalAngewandte Chemie International Editionde


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