Inprung, Nantachai, Ho, Hon Eong orcid.org/0000-0003-1037-2505, Rossi-Ashton, James A et al. (6 more authors) (2022) Indole-ynones as Privileged Substrates for Radical Dearomatizing Spirocyclization Cascades. Organic letters. pp. 668-674. ISSN 1523-7052
Abstract
Indole-ynones have been established as general substrates for radical dearomatizing spirocyclization cascade reactions. Five distinct and varied synthetic protocols have been developed─cyanomethylation, sulfonylation, trifluoromethylation, stannylation and borylation─using a variety of radical generation modes, ranging from photoredox catalysis to traditional AIBN methods. The simple and easily prepared indole-ynones can be used to rapidly generate diverse, densely functionalized spirocycles and have the potential to become routinely used to explore radical reactivity. Experimental and computational investigations support the proposed radical cascade mechanism and suggest that other new methods are now primed for development.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 2022 American Chemical Society. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number EPSRC EP/R013748/1 |
Depositing User: | Pure (York) |
Date Deposited: | 20 Jan 2022 09:40 |
Last Modified: | 26 Jan 2025 00:18 |
Published Version: | https://doi.org/10.1021/acs.orglett.1c04098 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1021/acs.orglett.1c04098 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:182749 |
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