Synthesis of Indenone Derivatives by Rh(III)-Catalyzed C–H Functionalization of Sulfoxonium Ylides with 1,3-Diynes
The transition-metal-catalyzed C–H functionalization of sulfoxonium ylides with alkynes formally participates in [4 + 2] annulations to deliver the naphthol scaffolds. In contrast, herein we disclose the first Rh(III)-catalyzed C–H activation, followed by redox-neutral [3 + 2] annulation of sulfoxo...
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Veröffentlicht in: | Organic letters 2022-05, Vol.24 (18), p.3395-3400 |
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Hauptverfasser: | , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | The transition-metal-catalyzed C–H functionalization of sulfoxonium ylides with alkynes formally participates in [4 + 2] annulations to deliver the naphthol scaffolds. In contrast, herein we disclose the first Rh(III)-catalyzed C–H activation, followed by redox-neutral [3 + 2] annulation of sulfoxonium ylides with 1,3-diynes, which delivers the alkynated indenone derivatives. This protocol features a good functional group tolerance, a broad substrate scope, moderate to excellent yields, and mild reaction conditions. The reaction mechanism was supported through ESI-HRMS by characterizing key intermediates in the catalytic cycle. |
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ISSN: | 1523-7060 1523-7052 |
DOI: | 10.1021/acs.orglett.2c01166 |