Donald, James Robert orcid.org/0000-0002-2176-4902 and Berrell, Sophie (2019) Radical cyanomethylation via vinyl azide cascade-fragmentation. Chemical Science. pp. 5832-5836. ISSN 2041-6539
Abstract
Herein, a novel methodology for radical cyanomethylation is described. The process is initiated by radical addition to the vinyl azide reagent 3-azido-2-methylbut-3-en-2-ol which triggers a cascade-fragmentation mechanism driven by the loss of dinitrogen and the stabilised 2-hydroxypropyl radical, ultimately effecting cyanomethylation. Cyanomethyl groups can be efficiently introduced into a range of substrates via trapping of α-carbonyl, heterobenzylic, alkyl, sulfonyl and aryl radicals, generated from a variety of functional groups under both photoredox catalysis and non-catalytic conditions. The value of this approach is exemplified by the late-stage cyanomethylation of pharmaceuticals.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 26 Sep 2022 15:50 |
Last Modified: | 06 Jan 2025 00:18 |
Published Version: | https://doi.org/10.1039/C9SC01370A |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1039/C9SC01370A |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:191267 |