CHIRILA, Paula G., ADAMS, Joshua, DIRJAL, Amir, HAMILTON, Alexander and WHITEOAK, Christopher (2018). Cp*Co(III)-Catalyzed coupling of benzamides with α,β-unsaturated carbonyl compounds: Preparation of aliphatic ketones and azepinones. Chemistry : A European Journal, 24 (14), 3584-3589.
![]() |
PDF
Hamilton-CpCoIII-CatalyzedCoupling(AM).pdf - Accepted Version Restricted to Repository staff only until 8 January 2019. All rights reserved. Download (595kB) |
![]() |
PDF
Supporting Information.pdf - Supplemental Material Restricted to Repository staff only until 8 January 2019. All rights reserved. Download (2MB) |
Abstract
A Cp*Co(III)-catalyzed C-H functionalization of benzamide substrates with α,β-unsaturated ketones has been optimized, providing a facile route towards aliphatic ketone products. When employing α,β-unsaturated aldehydes as coupling partners, under the optimized protocol, a cascade reaction forming azepinones has also been developed. Finally, DFT studies have demonstrated how stabilization of a metallo-enol intermediate when employing α,β-unsaturated ketones is the driving force leading to the observed aliphatic ketone product rather than olefinic products reported using α,β-unsaturated esters as coupling partners.
Item Type: | Article |
---|---|
Research Institute, Centre or Group: | Biomolecular Sciences Research Centre |
Identification Number: | 10.1002/chem.201705785 |
Depositing User: | Christopher Whiteoak |
Date Deposited: | 15 Jan 2018 15:43 |
Last Modified: | 18 Apr 2018 19:11 |
URI: | http://shura.shu.ac.uk/id/eprint/18217 |
Actions (login required)
![]() |
View Item |
Downloads
Downloads per month over past year