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Cycloaddition-based formal C-H alkynylation of isoindoles leading to the synthesis of air-stable fluorescent 1,3-dialkynylisoindoles. | LitMetric
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Cycloaddition-based formal C-H alkynylation of isoindoles leading to the synthesis of air-stable fluorescent 1,3-dialkynylisoindoles.

Toshimichi Ohmura Akihito Kijima Yusuke Komori Michinori Suginome

Org Lett

Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Katsura, Kyoto 615-8510, Japan.

Published: July 2013

Reaction of N-alkylisoindoles with (bromoethynyl)triisopropylsilane afforded 1,3-bis(triisopropylsilylethynyl) isoindoles in high yields. The formal C-H alkynylation proceeds under transition-metal-free conditions through [4 + 2] cycloaddition of the pyrrole ring of isoindole with bromoalkyne followed by ring-opening of the product.

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http://dx.doi.org/10.1021/ol401051dDOI Listing

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