Tosylhydrazide-induced 1,6-enyne radical cyclization under copper catalysis: access to 3,4-dihydronaphthalen-1(2H)-one derivatives
We describe an approach to access 4-aroyl-3-aryl-3,4-dihydronaphthalen-1(2H)-one derivatives in 41-79% yields through the Cu-catalyzed radical cyclization/desulfonylation of 1,6-enynes with tosylhydrazide under air conditions. This alternative desulfonylation strategy combines mild conditions, exter...
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| Hauptverfasser: | , , , |
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| Dokumenttyp: | Article (Journal) |
| Sprache: | Englisch |
| Veröffentlicht: |
20 September 2024
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| In: |
The journal of organic chemistry
Year: 2024, Jahrgang: 89, Heft: 18, Pages: 13575-13584 |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.4c01746 |
| Online-Zugang: | Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1021/acs.joc.4c01746
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| Verfasserangaben: | Yeganeh Sadat Hosseini Nasab, Saideh Rajai-Daryasarei, Frank Rominger, Saeed Balalaie |
| Zusammenfassung: | We describe an approach to access 4-aroyl-3-aryl-3,4-dihydronaphthalen-1(2H)-one derivatives in 41-79% yields through the Cu-catalyzed radical cyclization/desulfonylation of 1,6-enynes with tosylhydrazide under air conditions. This alternative desulfonylation strategy combines mild conditions, external oxidant-free processes, and sustainability, contributing to more environmentally friendly organic synthesis. The mechanistic studies showed that the CuCl/O2 combination serves as the source of the oxygen atom needed to form the C═O bond. The existence of tosylhydrazide is crucial for this conversion. |
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| Beschreibung: | Online veröffentlicht: 30. August 2024 Gesehen am 20.09.2024 |
| Beschreibung: | Online Resource |
| ISSN: | 1520-6904 |
| DOI: | 10.1021/acs.joc.4c01746 |