Katie Ruffell
Bismuth-Mediated α-Arylation of Acidic Diketones with ortho-Substituted Boronic Acids
Ruffell, Katie; Argent, Stephen P.; Ling, Kenneth B.; Ball, Liam T.
Authors
STEPHEN ARGENT stephen.argent@nottingham.ac.uk
Senior Research Fellow
Kenneth B. Ling
LIAM BALL Liam.Ball@nottingham.ac.uk
Associate Professor
Abstract
The α-arylation of cyclic and fluoroalkyl 1,3-diketones is made challenging by the highly stabilized nature of the corresponding enolates, and is especially difficult for sterically demanding aryl partners. As a general solution to this problem, we report the Bi-mediated oxidative coupling of acidic diones and ortho-substituted arylboronic acids. Starting from a bench-stable bismacycle precursor, a sequence of B-to-Bi transmetallation, oxidation and C−C bond formation furnishes the arylated diones. Development of methodology that tolerates both sensitive functionality and steric demand is supported by interrogation of key reactive intermediates. Application of our strategy to cyclic diones enables the concise synthesis of important agrochemical intermediates which were previously prepared using toxic Pb reagents. This methodology also enables the first ever arylation of fluoroalkyl diones which, upon condensation with hydrazine, provides direct access to valuable fluoroalkyl pyrazoles.
Citation
Ruffell, K., Argent, S. P., Ling, K. B., & Ball, L. T. (2022). Bismuth-Mediated α-Arylation of Acidic Diketones with ortho-Substituted Boronic Acids. Angewandte Chemie International Edition, 61(40), Article e202210840. https://doi.org/10.1002/anie.202210840
Journal Article Type | Article |
---|---|
Acceptance Date | Aug 10, 2022 |
Online Publication Date | Aug 11, 2022 |
Publication Date | Oct 4, 2022 |
Deposit Date | Aug 18, 2022 |
Publicly Available Date | Mar 29, 2024 |
Journal | Angewandte Chemie - International Edition |
Print ISSN | 1433-7851 |
Electronic ISSN | 1521-3773 |
Publisher | Wiley |
Peer Reviewed | Peer Reviewed |
Volume | 61 |
Issue | 40 |
Article Number | e202210840 |
DOI | https://doi.org/10.1002/anie.202210840 |
Keywords | General Chemistry; Catalysis |
Public URL | https://nottingham-repository.worktribe.com/output/10080650 |
Publisher URL | https://onlinelibrary.wiley.com/doi/10.1002/anie.202210840 |
Files
Angew Chem Int Ed - 2022 - Ruffell - Bismuth ? Mediated ? Arylation Of Acidic Diketones With Ortho ? Substituted Boronic Acids
(1.8 Mb)
PDF
Angew Chem Int Ed - 2022 - Ruffell - Bismuth‐Mediated ‐Arylation of Acidic Diketones with ortho‐Substituted Boronic Acids
(10.3 Mb)
PDF
Publisher Licence URL
https://creativecommons.org/licenses/by/4.0/
You might also like
Skeletal Editing: Interconversion of Arenes and Heteroarenes
(2023)
Journal Article
Umpolung Synthesis of Pyridyl Ethers by Bi(V)‐Mediated O‑Arylation of Pyridones
(2022)
Journal Article
Downloadable Citations
About Repository@Nottingham
Administrator e-mail: digital-library-support@nottingham.ac.uk
This application uses the following open-source libraries:
SheetJS Community Edition
Apache License Version 2.0 (http://www.apache.org/licenses/)
PDF.js
Apache License Version 2.0 (http://www.apache.org/licenses/)
Font Awesome
SIL OFL 1.1 (http://scripts.sil.org/OFL)
MIT License (http://opensource.org/licenses/mit-license.html)
CC BY 3.0 ( http://creativecommons.org/licenses/by/3.0/)
Powered by Worktribe © 2024
Advanced Search