Issue 35, 2021

Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate

Abstract

Isoindolinones are ubiquitous structural motifs in natural products and pharmaceuticals. Establishing an efficient method for structural modification of isoindolinones could significantly facilitate new drug development. Herein, we describe copper-promoted direct amidation of isoindolinone scaffolds mediated by sodium persulfate. The method exhibits mild reaction conditions and high site-selectivity, and enables the structural modification of the drug indobufen ester with various amides with yields of 49 to 98%. It is also gram-scalable. Additionally, the reaction mechanism appears to involve a radical and a carbocationic pathway.

Graphical abstract: Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate

Supplementary files

Article information

Article type
Paper
Submitted
31 May 2021
Accepted
09 Jul 2021
First published
12 Jul 2021

Org. Biomol. Chem., 2021,19, 7621-7626

Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate

H. Lai, J. Xu, J. Lin and D. Zha, Org. Biomol. Chem., 2021, 19, 7621 DOI: 10.1039/D1OB01054A

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