Cp*Co(III)-Catalyzed coupling of benzamides with α,β-unsaturated carbonyl compounds: Preparation of aliphatic ketones and azepinones

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.

Preview	PDF Hamilton-CpCoIII-CatalyzedCoupling(AM).pdf - Accepted Version All rights reserved. Download (595kB) | Preview
Preview	PDF Supporting Information.pdf - Supplemental Material All rights reserved. Download (2MB) | Preview

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 - Does NOT include content added after October 2018:	Biomedical Research Centre
Identification Number:	https://doi.org/10.1002/chem.201705785
Page Range:	3584-3589
Depositing User:	Christopher Whiteoak
Date Deposited:	15 Jan 2018 15:43
Last Modified:	18 Mar 2021 07:05
URI:	https://shura.shu.ac.uk/id/eprint/18217

Actions (login required)

View Item

Downloads

Publication Metrics