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Cobalt-catalyzed Wagner–Meerwein rearrangements with concomitant nucleophilic hydrofluorination
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dc.contributor.author | Hoogesteger, Reece H. | |
dc.contributor.author | Murdoch, Nicola | |
dc.contributor.author | Cordes, David B. | |
dc.contributor.author | Johnston, Craig Paterson | |
dc.date.accessioned | 2023-07-19T15:30:09Z | |
dc.date.available | 2023-07-19T15:30:09Z | |
dc.date.issued | 2023-08-28 | |
dc.identifier | 290052059 | |
dc.identifier | 372c442e-c6fe-4eae-9103-7e6fc746f48c | |
dc.identifier | 85165250562 | |
dc.identifier.citation | Hoogesteger , R H , Murdoch , N , Cordes , D B & Johnston , C P 2023 , ' Cobalt-catalyzed Wagner–Meerwein rearrangements with concomitant nucleophilic hydrofluorination ' , Angewandte Chemie International Edition , vol. 62 , no. 35 , e202308048 . https://doi.org/10.1002/anie.202308048 | en |
dc.identifier.issn | 1433-7851 | |
dc.identifier.other | RIS: urn:399A7CA135EA96D96AE40383A0F9A2C8 | |
dc.identifier.other | ORCID: /0000-0003-2459-1872/work/139156455 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/139156719 | |
dc.identifier.uri | https://hdl.handle.net/10023/27990 | |
dc.description | Funding: The authors acknowledge funding from the Royal Society (University Research Fellowship URF\R1\180017 (CPJ) and associated Enhancement Award RGF\EA\181022 (CPJ and RHH)), and the EaSI-CAT Centre for Doctoral Training (RHH and NM). | en |
dc.description.abstract | We report a cobalt-catalyzed Wagner-Meerwein rearrangement of gem-disubstituted allylarenes that generates fluoroalkane products with isolated yields up to 84%. Modification of the counteranion of the N-fluoropyridinium oxidant suggests the substrates undergo nucleophilic fluorination during the reaction. Subjecting the substrates to other known metal-mediated hydrofluorination procedures did not lead to observable 1,2-aryl migration. Thus, indicating the unique ability of these cobalt-catalyzed conditions to generate a sufficiently reactive electrophilic intermediate capable of promoting this Wagner-Meerwein rearrangement. | |
dc.format.extent | 7 | |
dc.format.extent | 8757637 | |
dc.language.iso | eng | |
dc.relation.ispartof | Angewandte Chemie International Edition | en |
dc.subject | Cobalt catalysis | en |
dc.subject | Hydrofluorination | en |
dc.subject | Wagner-Meerwein | en |
dc.subject | Cations | en |
dc.subject | Phenonium Ion | en |
dc.subject | DAS | en |
dc.subject | MCC | en |
dc.title | Cobalt-catalyzed Wagner–Meerwein rearrangements with concomitant nucleophilic hydrofluorination | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Royal Society | en |
dc.contributor.sponsor | The Royal Society | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1002/anie.202308048 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | URF/R1/180017 | en |
dc.identifier.grantnumber | RGF\EA\181022 | en |
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