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dc.contributor.authorMorrill, Charlotte
dc.contributor.authorGillespie, James E.
dc.contributor.authorPhipps, Robert J.
dc.date.accessioned2022-07-07T14:00:06Z
dc.date.available2022-07-07T14:00:06Z
dc.date.issued2022-07-07
dc.date.submitted2022-03-17
dc.identifier.citationAngewandte Chemie, article-number e202204025
dc.identifier.issn0044-8249
dc.identifier.issn1521-3757
dc.identifier.otherange202204025
dc.identifier.urihttps://www.repository.cam.ac.uk/handle/1810/338874
dc.description.abstractAbstract: Ortho‐sulfonyl anilines are important building blocks for a range of applications. We report the discovery of an aromatic rearrangement reaction of O‐(arenesulfonyl)hydroxylamines which leads directly to ortho‐sulfonyl anilines through formation of a new C−N bond with excellent levels of regiocontrol for the ortho position(s) over all others. We establish that the rearrangement is proceeding through an intermolecular mechanism and propose that the regiocontrol observed is the result of attractive non‐covalent interactions occurring during the C−N bond‐forming step. Importantly, this method is complementary to classical aniline sulfonation in terms of the variously substituted regioisomers that can be obtained and it is also applicable to O‐(benzylsulfonyl) hydroxylamines.
dc.languageen
dc.subjectZuschrift
dc.subjectZuschriften
dc.subjectArene Amination
dc.subjectIon-Pairing
dc.subjectNon-Covalent Interactions
dc.subjectRadical Reactions
dc.subjectRegioselectivity
dc.titleAn Aminative Rearrangement of O ‐(Arenesulfonyl)hydroxylamines: Facile Access to ortho ‐Sulfonyl Anilines
dc.typeOther
dc.date.updated2022-07-07T14:00:06Z
dc.identifier.doi10.17863/CAM.86280
rioxxterms.versionofrecord10.1002/ange.202204025
rioxxterms.versionAO
rioxxterms.versionVoR
rioxxterms.licenseref.urihttp://creativecommons.org/licenses/by/4.0/
dc.contributor.orcidPhipps, Robert J. [0000-0002-7383-5469]
pubs.funder-project-idThe Royal Society (URF\R\191003, RGF\EA\180005)
pubs.funder-project-idEngineering and Physical Sciences Research Council (EP/S03269X/1)
pubs.funder-project-idH2020 European Research Council (757381)


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