Single-Carbon Insertion into Single C–C Bonds with Diazirines
A novel platform for the skeletal editing of single C–C bonds via a single-carbon insertion has been developed using diazirines. This strategy involves the photogeneration of arylchlorocarbenes as carbynoid species that undergo site-selective carbene insertion into tertiary C–H bonds and a subsequen...
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| Veröffentlicht in: | Journal of the American Chemical Society 2025-01, Vol.147 (1), p.57-62 |
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| container_title | Journal of the American Chemical Society |
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| creator | Alfonso, Valero G. de la Vega-Hernández, Karen Suero, Marcos G. |
| description | A novel platform for the skeletal editing of single C–C bonds via a single-carbon insertion has been developed using diazirines. This strategy involves the photogeneration of arylchlorocarbenes as carbynoid species that undergo site-selective carbene insertion into tertiary C–H bonds and a subsequent Wagner–Meerwein rearrangement promoted by a silver salt. Our skeletal editing strategy based on a formal selective carbyne C–C bond insertion has been demonstrated in six core-to-core conversions, including linear and cyclic benzylic substrates, alkanes and late-stage functionalizations. |
| doi_str_mv | 10.1021/jacs.4c12632 |
| format | Article |
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| ispartof | Journal of the American Chemical Society, 2025-01, Vol.147 (1), p.57-62 |
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| language | eng |
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| source | American Chemical Society Journals |
| subjects | Communication |
| title | Single-Carbon Insertion into Single C–C Bonds with Diazirines |
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