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Cp*Co(III)‐Catalyzed Coupling of Benzamides with α,β‐Unsaturated Carbonyl Compounds: Preparation of Aliphatic Ketones and Azepinones
Author(s) -
Chirila Paula G.,
Adams Joshua,
Dirjal Amir,
Hamilton Alex,
Whiteoak Christopher J.
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201705785
Subject(s) - catalysis , chemistry , coupling (piping) , ketone , organic chemistry , medicinal chemistry , combinatorial chemistry , materials science , metallurgy
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.