Construction of Highly Functionalized Xanthones via Rh-Catalyzed Cascade C–H Activation/O‑Annulation

A facile and efficient strategy for obtaining functionalized and multihydroxylated xanthones via Rh catalysis under redox-neutral conditions is developed. Diverse salicylaldehydes bearing heterocycles, aromatics, and fused aromatics can be rapidly coupled with 1,4-benzoquinones or 1,4-hydroquinones...

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Bibliographic Details
Published in:Organic letters 2021-04, Vol.23 (7), p.2465-2470
Main Authors: Nale, Sagar D, Maiti, Debabrata, Lee, Yong Rok
Format: Article
Language:English
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Summary:A facile and efficient strategy for obtaining functionalized and multihydroxylated xanthones via Rh catalysis under redox-neutral conditions is developed. Diverse salicylaldehydes bearing heterocycles, aromatics, and fused aromatics can be rapidly coupled with 1,4-benzoquinones or 1,4-hydroquinones to afford valuable xanthones via cascade C–H/O–H functionalization and annulation. This protocol provides a rapid synthetic approach to obtain biologically active materials through late-stage functionalization and prepares natural products such as subelliptenone, pruniflorone N, and ravenelin.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c00391