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.

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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:	https://doi.org/10.1002/chem.201705785
Depositing User:	Christopher Whiteoak
Date Deposited:	15 Jan 2018 15:43
Last Modified:	21 Jul 2018 19:16
URI:	http://shura.shu.ac.uk/id/eprint/18217

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