Clarke, Aimee K., Lynam, Jason M. orcid.org/0000-0003-0103-9479, Taylor, Richard John Kenneth orcid.org/0000-0002-5880-2490 et al. (1 more author) (2018) "Back-to-Front" Indole Synthesis using Silver(I) Catalysis:Unexpected C-3 Pyrrole Activation Mode Supported by DFT. ACS Catalysis. pp. 6844-6850. ISSN 2155-5435
Abstract
An efficient silver(I)-catalyzed method is reported for the synthesis of substituted indoles, most notably 5-hydroxy-derivatives, via π-acidic alkyne activation. Most methods for the preparation of indoles involve annulation of a benzene precursor, but the method reported herein is unusual in that pyrrole precursors are used. Density Functional Theory (DFT) studies suggest that these reactions proceed via initial activation of the pyrrole C-3 position before undergoing subsequent rearrangement, contradicting the conventional wisdom that pyrroles are more nucleophilic through C-2.
Metadata
Item Type: | Article |
---|---|
Authors/Creators: |
|
Copyright, Publisher and Additional Information: | © 2018 American Chemical Society. |
Keywords: | alkynes,cyclization,indoles,silver(I),spirocycles |
Dates: |
|
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: | 17 Jul 2018 09:30 |
Last Modified: | 02 Apr 2025 23:13 |
Published Version: | https://doi.org/10.1021/acscatal.8b00745 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1021/acscatal.8b00745 |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:133416 |
Downloads
Filename: Aimee_indole_paper_version_18_revision_3_.docx
Description: Aimee_indole_paper_version_18_revision_3_