Rhodium-Catalyzed Direct Vinylene Annulation of 2-Aryloxazolines and Cascade Ring-Opening Using a Vinyl Selenone

Junya Kitano; Yuji Nishii; Koji Hirano; Masahiro Miura

doi:10.1055/a-2214-5299

Synlett, Table of Contents

Synlett 2024; 35(11): 1265-1268
DOI: 10.1055/a-2214-5299

cluster

Japan/Netherlands Gratama Workshop

Rhodium-Catalyzed Direct Vinylene Annulation of 2-Aryloxazolines and Cascade Ring-Opening Using a Vinyl Selenone

Authors

Junya Kitano

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Yuji Nishii ∗

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

^bCenter for Future Innovation, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan
Koji Hirano

^aDepartment of Applied Chemistry, Graduate School of Engineering, Osaka University, Suita, Osaka 565-0871, Japan

^cInnovative Catalysis Science Division, Institute for Open and Transitionary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan
Masahiro Miura ∗

^cInnovative Catalysis Science Division, Institute for Open and Transitionary Research Initiatives (ICS-OTRI), Osaka University, Suita, Osaka 565-0871, Japan

Abstract

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Abstract

Over the past two decades, transition-metal-catalyzed C–H activation and the subsequent oxidative cyclization with alkynes or their surrogates has emerged as a powerful synthetic tool for fused heteroaromatics. We report a Rh(III)-catalyzed annulation and ring-opening cascade reaction with 2-aryloxazolines. By utilizing a vinyl selenone as an oxidizing acetylene surrogate, the target three-component coupling products were obtained in high yields without using a stoichiometric amount of external oxidant.

Key words

C–H bond activation - oxazolines - annulation - rhodium catalysis - vinylselenones - cascade reaction

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References

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Supplementary Material

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