Liddon, John T.R. orcid.org/0000-0002-5287-9817, Rossi-Ashton, James A., Clarke, Aimee K. et al. (3 more authors) (Accepted: 2018) Divergent Reactivity of Indole-Tethered Ynones with Silver(I) and Gold(I) Catalysts:A Combined Synthetic and Computational Study. SYNTHESIS-STUTTGART. ISSN 0039-7881 (In Press)
Abstract
A combined synthetic and computational (DFT) study has been performed to account for the divergent reactivity of indole-tethered ynones when treated with Ag(I) and Au(I) catalysts. The two catalyst systems deliver spirocyclic indolenines and carbazoles, respectively, from the same precursors, with the reaction outcomes believed to be a result of differences in the rates of a key protodemetalation step. A ring-opening/ring-closing isomerisation process is proposed to enable the interconversion of spirocyclic and C-2 annulated indole intermediates, in contrast to the 1,2-migration mechanism tentatively proposed in previous studies.
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Copyright, Publisher and Additional Information: | © Georg Thieme Verlag Stuttgart. 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 |
Keywords: | carbazoles,catalysis,gold,indoles,silver,spirocycles,ynones |
Dates: |
|
Institution: | The University of York |
Academic Units: | The University of York The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number EPSRC EP/R013748/1 EPSRC EP/N035119/1 |
Depositing User: | Pure (York) |
Date Deposited: | 17 Jul 2018 13:50 |
Last Modified: | 07 Dec 2024 00:15 |
Published Version: | https://doi.org/10.1055/s-0037-1610181 |
Status: | In Press |
Refereed: | Yes |
Identification Number: | 10.1055/s-0037-1610181 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:133441 |
Download
Filename: Silver_vs_Gold_Synthesis_Special_issue_version_7_revision.docx
Description: Silver_vs_Gold_Synthesis_Special_issue_version_7_revision