Copper-promoted direct amidation of isoindolinone scaffolds by sodium persulfate. Issue 35 (26th July 2021)

• Record Type: Journal Article
• Authors: Lai, Huifang; Xu, Jiexin; Lin, Jin; Zha, Daijun
• Is Part Of: Organic & biomolecular chemistry. Volume 19:Issue 35(2021)
• Page Start: 7621
• Page End: 7626
• Publication Date: 2021-07-26
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d1ob01054a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : We described a copper-promoted direct amidation of isoindolinone scaffolds mediated by sodium persulfate. The amides, including primary and secondary amides, can be installed on isoindolinones in moderate to excellent yields by this method. 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.