Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes

Teppei Noguchi; Yuji Nishii; Masahiro Miura

doi:10.1055/s-0037-1610376

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CC BY ND NC 4.0 · Synthesis 2019; 51(01): 258-270
DOI: 10.1055/s-0037-1610376

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Rhodium-Catalyzed Cascade Annulative Coupling of 3,5-Diarylisoxazoles with Alkynes

Teppei Noguchi

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan Email: miura@chem.eng.osaka-u.ac.jp

,

Yuji Nishii*

^bFrontier Research Base for Global Young Researchers, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan Email: y_nishii@chem.eng.osaka-u.ac.jp

,

Masahiro Miura *

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan Email: miura@chem.eng.osaka-u.ac.jp

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Abstract

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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 compounds

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