A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of N-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 BF3·OEt2 at room temperature. For most of the olefins, the reactions afforded the Csp3–Csp2 cross-coupling products, but for the α-methylstyrene and 1-hexene, the Csp3–Csp3 cross-coupling products were obtained.

Keywords

• 3-(1-alkenyl)isoindol-1-ones
• 5-(1-alkenyl)pyrrol-2-ones
• coupling reaction
• 2,3-dihydro-3-hydroxyisoindol-1-one
• 2,5-dihydro-5-hydroxypyrrol-2-one
• N-acyliminium ions