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
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 mos...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2012-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.8.21 |
| _version_ | 1831670407493582848 |
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| author | Nianhong Lu Lihong Wang Zhanshan Li Wei Zhang |
| author_facet | Nianhong Lu Lihong Wang Zhanshan Li Wei Zhang |
| author_sort | Nianhong Lu |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-19T23:17:04Z |
| format | Article |
| id | doaj.art-6297a1abc64641d8a83ceff67d65d454 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-19T23:17:04Z |
| publishDate | 2012-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-6297a1abc64641d8a83ceff67d65d4542022-12-21T20:02:04ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972012-02-018119220010.3762/bjoc.8.211860-5397-8-21A 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 olefinsNianhong Lu0Lihong Wang1Zhanshan Li2Wei Zhang3State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China; Fax: +86 (931) 8625657State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China; Fax: +86 (931) 8625657State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China; Fax: +86 (931) 8625657State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, China; Fax: +86 (931) 8625657A 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.https://doi.org/10.3762/bjoc.8.213-(1-alkenyl)isoindol-1-ones5-(1-alkenyl)pyrrol-2-onescoupling reaction2,3-dihydro-3-hydroxyisoindol-1-one2,5-dihydro-5-hydroxypyrrol-2-oneN-acyliminium ions |
| spellingShingle | Nianhong Lu Lihong Wang Zhanshan Li Wei Zhang 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 Beilstein Journal of Organic Chemistry 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 |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | 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 |
| topic | 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 |
| url | https://doi.org/10.3762/bjoc.8.21 |
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