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Rhodium-Catalyzed Isoquinoline Synthesis Using Vinyl Selenone as Oxidizing Acetylene Surrogate

Ayumi Inami, Yuji Nishii*, Koji Hirano and Masahiro Miura*

*Osaka University, Suita, Osaka 565-0871, Japan, Email: y_nishiichem.eng.osaka-u.ac.jp, miurachem.eng.osaka-u.ac.jp

A. Inami, Y. Nishii, K. Hirano, M. Miura, Org. Lett., 2023, 25, 3206-3209.

DOI: 10.1021/acs.orglett.3c00826


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Abstract

Vinyl selenone is an effective acetylene surrogate for a Rh-catalyzed annulative coupling to provide 3,4-nonsubstituted isoquinolines under mild conditions. The Se fragment can be recovered as diselenide and recycled. The product can readily be converted to 1-aminoisoquinolines.

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proposed mechanism



Key Words

isoquinolines


ID: J54-Y2023