Silver-Catalyzed Direct Synthesis of Trifluoromethylated Enaminopyridines and Isoquinolinones Employing Trifluorodiazoethane
This Letter reports a Ag-catalyzed three-component approach for the N-alkenylation of 2-aminopyridines employing aldehydes and trifluorodiazoethane. Unlike the known reactions of trifluorodiazoethane with imines, which generate Mannich adducts, aziridines, or triazolines depending on the substrates...
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| Published in: | Organic letters Vol. 23; no. 15; pp. 5815 - 5820 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
American Chemical Society
06-08-2021
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| Online Access: | Get full text |
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| Summary: | This Letter reports a Ag-catalyzed three-component approach for the N-alkenylation of 2-aminopyridines employing aldehydes and trifluorodiazoethane. Unlike the known reactions of trifluorodiazoethane with imines, which generate Mannich adducts, aziridines, or triazolines depending on the substrates and conditions, this reaction, after Mannich addition, proceeds via a carbene formation and 1,2-aryl migration sequence to afford (E)-enaminopyridines. This surprising selectivity, which is effective for a wide range of aldehydes and 2-aminopyridines, has been subsequently explored to access trifluoromethylated isoquinolinones. |
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| Bibliography: | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ISSN: | 1523-7060 1523-7052 |
| DOI: | 10.1021/acs.orglett.1c01969 |