Catalytic generation of arynes and trapping by nucleophilic addition and iodination

T Hamura, Y Chuda, Y Nakatsuji…

Index: Hamura, Toshiyuki; Chuda, Yu; Nakatsuji, Yuya; Suzuki, Keisuke Angewandte Chemie - International Edition, 2012 , vol. 51, # 14 p. 3368 - 3372

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Citation Number: 34

Abstract

Benzyne is a highly reactive species with broad synthetic potential.[1] Among various methods for generating this species through elimination of 1, 2-difunctionalized benzene precursors,[2] we have exploited 2-iodoaryl triflate (1) as an excellent benzyne precursor, which is immediately converted into benzyne even at À958C upon reaction with nBuLi (Scheme 1).[3] Two rapid consecutive processes are relevant:

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