Organic letters

Cycloaddition-based Formal C–H Alkynylation of Isoindoles Leading to the Synthesis of Air-stable Fluorescent 1, 3-Dialkynylisoindoles

T Ohmura, A Kijima, Y Komori, M Suginome

Index: Ohmura, Toshimichi; Kijima, Akihito; Komori, Yusuke; Suginome, Michinori Organic Letters, 2013 , vol. 15, # 14 p. 3510 - 3513

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Citation Number: 7

Abstract

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.