Cobalt-catalyzed Wagner–Meerwein rearrangements with concomitant nucleophilic hydrofluorination
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.
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
Publication
Angewandte Chemie International Edition
Status
Peer reviewed
ISSN
1433-7851Type
Journal article
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).Collections
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.