Generation of Benzyne Species from Diphenylphosphoryl Derivatives: Simultaneous Exchange of Three Functional Groups

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dc.contributor.authorEvgueni Gorobets
dc.contributor.authorMasood Parvez
dc.contributor.authorDarren J. Derksen
dc.contributor.authorBrian A. Keay
dc.date.accessioned2024-04-10T21:18:08Z
dc.date.available2024-04-10T21:18:08Z
dc.date.issued2016-05-16
dc.description.abstractInteraction of (2‐diphenylphosphoryl‐3‐iodo‐4‐methoxy‐phenyl) methanol with NaH in DMF at ambient temperature results in the generation of benzyne intermediates that can be trapped by furan or DMF. Trapping with DMF forms 3‐(dimethylaminomethyl)‐2‐hydroxy‐6‐methoxybenzaldehyde demonstrating the simultaneous exchange of three functionalities in a single step. The presence of the alkoxy substituent adjacent to iodine is critical for high regioselectivity addition of DMF. The corresponding bromide or triflate can be used in place of the iodide with equal efficiency. This methodology was used to synthesize the reported structure of gigasol and leading to a structural reassignment of this biscoumarin natural product.
dc.description.grantingagencyNatural Sciences and Engineering Research Council (NSERC)
dc.identifier.citationGeneration of Benzyne Species from Diphenylphosphoryl Derivatives: Simultaneous Exchange of Three Functional Groups—Gorobets—2016—Chemistry – A European Journal—Wiley Online Library. (n.d.). Retrieved April 10, 2024, from https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/chem.201601370
dc.identifier.doihttps://doi.org/10.1002/chem.201601370
dc.identifier.issn0947-6539
dc.identifier.issn1521-3765
dc.identifier.urihttps://hdl.handle.net/1880/118364
dc.identifier.urihttps://doi.org/10.11575/PRISM/43206
dc.language.isoenen
dc.publisherEuropean Chemical Societies Publishing
dc.publisher.facultyScienceen
dc.publisher.hasversionacceptedVersion
dc.publisher.institutionUniversity of Calgaryen
dc.publisher.policyhttps://authorservices.wiley.com/author-resources/Journal-Authors/licensing/self-archiving.html
dc.relation.ispartofChemistry – A European Journal
dc.rightsUnless otherwise indicated, this material is protected by copyright and has been made available with authorization from the copyright owner. You may use this material in any way that is permitted by the Copyright Act or through licensing that has been assigned to the document. For uses that are not allowable under copyright legislation or licensing, you are required to seek permission.en
dc.titleGeneration of Benzyne Species from Diphenylphosphoryl Derivatives: Simultaneous Exchange of Three Functional Groups
dc.typeArticle
oaire.citation.issue25
oaire.citation.volume22
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