Chameleonic Reactivity of Imidoyl Sulfoxonium Ylides: Access to Functionalized Pyrroles and Dihydro-pyridines
We have found a chameleonic reactivity of imidoyl sulfoxonium ylides. On the one hand, imidoyl sulfoxonium ylides react with electron-deficient reagents, such as alkynyl esters, to lead to the formation of 1,2-dihydro-pyridines. The methyl group attached to the sulfur atom acts as a methylene donor....
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| Published in: | Organic letters Vol. 26; no. 1; pp. 62 - 67 |
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| Main Authors: | , , |
| Format: | Journal Article |
| Language: | English |
| Published: |
United States
American Chemical Society
12-01-2024
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| Online Access: | Get full text |
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| Summary: | We have found a chameleonic reactivity of imidoyl sulfoxonium ylides. On the one hand, imidoyl sulfoxonium ylides react with electron-deficient reagents, such as alkynyl esters, to lead to the formation of 1,2-dihydro-pyridines. The methyl group attached to the sulfur atom acts as a methylene donor. On the other hand, imidoyl sulfoxonium ylides react with pyridinium 1,4-zwitterionic thiolates, which leads to the formation of functionalized pyrroles. Both transformations feature mild reaction conditions and good functional group tolerance. |
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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.3c03625 |