Issue 19, 2020

Coupling of amides with ketones via C–N/C–H bond cleavage: a mild synthesis of 1,3-diketones

Abstract

A variety of aryl and alkyl-substituted tertiary amides react with ketones in the presence of LiHMDS and a variety of primary and secondary amides in one pot to give the corresponding 1,3-diketone products in good to excellent yields via C–N cleavage of amides and deprotonation of ketones. The reaction was conducted at room temperature under transition-metal-free conditions. N-Tosyl-, N-triflyl-, N-mesyl-, and N-Boc-substituted tertiary amides including N-benzoyl saccharin and N-benzoyl succinimide showed good activity in the reaction. The broad scope, good functional group tolerance of substrates and gram-scale synthesis showed the great importance and potential of this protocol in organic synthesis and industrial manufacture.

Graphical abstract: Coupling of amides with ketones via C–N/C–H bond cleavage: a mild synthesis of 1,3-diketones

Supplementary files

Article information

Article type
Research Article
Submitted
04 Jul 2020
Accepted
10 Aug 2020
First published
11 Aug 2020

Org. Chem. Front., 2020,7, 2931-2937

Coupling of amides with ketones via C–N/C–H bond cleavage: a mild synthesis of 1,3-diketones

J. Chen, Y. Xia and S. Lee, Org. Chem. Front., 2020, 7, 2931 DOI: 10.1039/D0QO00797H

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