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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 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 ?-methylstyrene and 1-hexene, the C(sp3)-C(sp3) cross-coupling products were obtained.

SUBMITTER: Lu N

PROVIDER: S-EPMC3302081 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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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.

Lu Nianhong N Wang Lihong L Li Zhanshan Z Zhang Wei W

Beilstein journal of organic chemistry 20120206

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. ...[more]

PMID: 22423287

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