A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of <i>N</i>-acyliminium ions with unactivated olefins

Abstract

A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones has been achieved by the coupling reactions of N-acyliminium ions produced from 3-hydroxyisoindol-1-ones or 5-hydroxy-1-pyrrol-2-ones with unactivated olefins in the presence of BF(3)·OEt(2) at room temperature. For most of the olefins, the reactions afforded the C(sp3)-C(sp2) cross-coupling products, but for the α-methylstyrene and 1-hexene, the C(sp3)-C(sp3) cross-coupling products were obtained.