Beilstein Journal of Organic Chemistry (Feb 2012)
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.
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