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
Hauptverfasser: Kumar, Sanjeev, Nunewar, Saiprasad, Sabbi, Tharun Kumar, Kanchupalli, Vinaykumar
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Sprache:eng
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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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01166