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DOI: 10.1055/s-0037-1610376
Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes
This work was supported by JSPS KAKENHI JP 17H06092 (Grant-in-Aid for Specially Promoted Research) to M.M.Publication History
Received: 07 August 2018
Accepted after revision: 28 August 2018
Publication Date:
19 September 2018 (online)


Published as part of the 50 Years SYNTHESIS – Golden Anniversary Issue
Abstract
A rhodium-catalyzed cascade annulative coupling of 3,5-diarylisoxazoles with three equivalents of an alkyne proceeds smoothly in the presence of a Cu(II) oxidant, where the sequential construction of isoquinoline and naphtho[1,8-bc]pyran frameworks connected by a biaryl linkage is achieved by a single operation. Most of the obtained polycyclic compounds exhibit visible fluorescence in both the solution and the solid state. The hexaphenylated isoquinoline-naphthopyran conjugate (R = Ph) as a representative product shows a green emission which can be turned off by making an isoquinolinium salt with an acid. The emission is also reversibly turned on by treatment with a base.
Key words
C–H activation - annulative coupling - isoquinoline - rhodium catalyst - polyaromatic compoundsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610376.
- Supporting Information