A Unified Strategy Toward 5‐, 6‐, and 7‐Membered Nitrogen Heterocycles Through Free Radical then Metal‐Mediated Functionalization of Ene‐carbamates
Free‐radical carbo‐alkenylation of N‐aryl‐, N‐benzyl‐, and N‐phenethyl‐ene‐carbamates with a disulfone provides vinyl sulfones which may then be functionalized and engaged in Heck‐type coupling to furnish highly substituted 5‐, 6‐ and 7‐membered nitrogen heterocycles. Grignard‐mediated cyclization s...
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| Published in: | Advanced synthesis & catalysis Vol. 359; no. 18; pp. 3217 - 3225 |
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| Main Authors: | , , , , , |
| Format: | Journal Article |
| Language: | English |
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18-09-2017
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| Abstract | Free‐radical carbo‐alkenylation of N‐aryl‐, N‐benzyl‐, and N‐phenethyl‐ene‐carbamates with a disulfone provides vinyl sulfones which may then be functionalized and engaged in Heck‐type coupling to furnish highly substituted 5‐, 6‐ and 7‐membered nitrogen heterocycles. Grignard‐mediated cyclization starting from the same substrates further allowed a nucleophilic cascade process, affording a straightforward access to hydrocarbazoles, which may be regarded as potent intermediates for the synthesis of alkaloids of the Aspidosperma family. |
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| AbstractList | Free‐radical carbo‐alkenylation of N‐aryl‐, N‐benzyl‐, and N‐phenethyl‐ene‐carbamates with a disulfone provides vinyl sulfones which may then be functionalized and engaged in Heck‐type coupling to furnish highly substituted 5‐, 6‐ and 7‐membered nitrogen heterocycles. Grignard‐mediated cyclization starting from the same substrates further allowed a nucleophilic cascade process, affording a straightforward access to hydrocarbazoles, which may be regarded as potent intermediates for the synthesis of alkaloids of the Aspidosperma family. Free-radical carbo-alkenylation of N-aryl, N-benzyl, and N-phenethyl-ene-carbamates with a disulfone provides vinylsulfones which may then be functionalized and engaged in Heck-type coupling to furnish highly substituted 5-, 6-and 7-membered nitrogen heterocycles. Grignardmediated cyclization starting from the same substrates further allowed a nucleophilic cascade process, affording a straightforward access to hydrocarbazoles, which may be regarded as potent intermediates for the synthesis of alkaloids of the aspidosperma family. Free‐radical carbo‐alkenylation of N ‐aryl‐, N ‐benzyl‐, and N ‐phenethyl‐ene‐carbamates with a disulfone provides vinyl sulfones which may then be functionalized and engaged in Heck‐type coupling to furnish highly substituted 5‐, 6‐ and 7‐membered nitrogen heterocycles. Grignard‐mediated cyclization starting from the same substrates further allowed a nucleophilic cascade process, affording a straightforward access to hydrocarbazoles, which may be regarded as potent intermediates for the synthesis of alkaloids of the Aspidosperma family. magnified image |
| Author | Beniazza, Redouane Poittevin, Clément Robert, Frédéric Lusseau, Jonathan Massip, Stéphane Landais, Yannick |
| Author_xml | – sequence: 1 givenname: Redouane surname: Beniazza fullname: Beniazza, Redouane organization: University of Bordeaux – sequence: 2 givenname: Clément surname: Poittevin fullname: Poittevin, Clément organization: University of Bordeaux – sequence: 3 givenname: Jonathan surname: Lusseau fullname: Lusseau, Jonathan organization: University of Bordeaux – sequence: 4 givenname: Stéphane surname: Massip fullname: Massip, Stéphane – sequence: 5 givenname: Frédéric surname: Robert fullname: Robert, Frédéric organization: University of Bordeaux – sequence: 6 givenname: Yannick surname: Landais fullname: Landais, Yannick email: yannick.landais@u-bordeaux.fr organization: University of Bordeaux |
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| Keywords | Heck reaction Heterocycle Grignard Cyclization Vinylsulfones |
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| Snippet | Free‐radical carbo‐alkenylation of N‐aryl‐, N‐benzyl‐, and N‐phenethyl‐ene‐carbamates with a disulfone provides vinyl sulfones which may then be functionalized... Free‐radical carbo‐alkenylation of N ‐aryl‐, N ‐benzyl‐, and N ‐phenethyl‐ene‐carbamates with a disulfone provides vinyl sulfones which may then be... Free-radical carbo-alkenylation of N-aryl, N-benzyl, and N-phenethyl-ene-carbamates with a disulfone provides vinylsulfones which may then be functionalized... |
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| SubjectTerms | Alkaloids Aromatic compounds Carbamates (tradename) Chemical Sciences cyclization Grignard reagents Heck reaction heterocycles Nitrogen Organic chemistry radical reaction Substrates Sulfones vinyl sulfones |
| Title | A Unified Strategy Toward 5‐, 6‐, and 7‐Membered Nitrogen Heterocycles Through Free Radical then Metal‐Mediated Functionalization of Ene‐carbamates |
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