A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates
An intermolecular radical addition, using photoredox catalysis, to allenamides and allencarbamates is reported. This transformation synthesizes N-acyl-N’-aryl-N,N’-allylaminals, and proceeds by a conjugated N-acyliminium intermediate that previously has principally been generated by electrophilic ac...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2020-08-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.16.165 |
| _version_ | 1819062263070326784 |
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| author | Olusesan K. Koleoso Matthew Turner Felix Plasser Marc C. Kimber |
| author_facet | Olusesan K. Koleoso Matthew Turner Felix Plasser Marc C. Kimber |
| author_sort | Olusesan K. Koleoso |
| collection | DOAJ |
| description | An intermolecular radical addition, using photoredox catalysis, to allenamides and allencarbamates is reported. This transformation synthesizes N-acyl-N’-aryl-N,N’-allylaminals, and proceeds by a conjugated N-acyliminium intermediate that previously has principally been generated by electrophilic activation methods. The radical adds to the central carbon of the allene giving a conjugated N-acyliminium that undergoes nucleophilic addition by arylamines and alcohols. |
| first_indexed | 2024-12-21T14:56:00Z |
| format | Article |
| id | doaj.art-59e45f281c354efca5c786957c797f51 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-21T14:56:00Z |
| publishDate | 2020-08-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-59e45f281c354efca5c786957c797f512022-12-21T18:59:46ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972020-08-011611983199010.3762/bjoc.16.1651860-5397-16-165A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamatesOlusesan K. Koleoso0Matthew Turner1Felix Plasser2Marc C. Kimber3School of Science, Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UKSchool of Science, Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UKSchool of Science, Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UKSchool of Science, Department of Chemistry, Loughborough University, Loughborough, LE11 3TU, UKAn intermolecular radical addition, using photoredox catalysis, to allenamides and allencarbamates is reported. This transformation synthesizes N-acyl-N’-aryl-N,N’-allylaminals, and proceeds by a conjugated N-acyliminium intermediate that previously has principally been generated by electrophilic activation methods. The radical adds to the central carbon of the allene giving a conjugated N-acyliminium that undergoes nucleophilic addition by arylamines and alcohols.https://doi.org/10.3762/bjoc.16.165allenamidealleneintermolecularn-acyliminiumphotoredox |
| spellingShingle | Olusesan K. Koleoso Matthew Turner Felix Plasser Marc C. Kimber A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates Beilstein Journal of Organic Chemistry allenamide allene intermolecular n-acyliminium photoredox |
| title | A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates |
| title_full | A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates |
| title_fullStr | A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates |
| title_full_unstemmed | A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates |
| title_short | A complementary approach to conjugated N-acyliminium formation through photoredox-catalyzed intermolecular radical addition to allenamides and allencarbamates |
| title_sort | complementary approach to conjugated n acyliminium formation through photoredox catalyzed intermolecular radical addition to allenamides and allencarbamates |
| topic | allenamide allene intermolecular n-acyliminium photoredox |
| url | https://doi.org/10.3762/bjoc.16.165 |
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