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Synthesis of Substituted Indoles from 2-Azidoacrylates and ortho-Silyl Aryltriflates

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posted on 15.10.2010, 00:00 by Deng Hong, Zhengbo Chen, Xufeng Lin, Yanguang Wang
2-Azidoacrylates react with benzynes in the presence of PPh3 and CsF to afford substituted indoles in good yields. The reaction involves the formation of iminophosphorane and benzyne and a subsequent double cyclization/hydrolysis/air-oxidation cascade. This methodology was utilized to synthesize 10H-indolo[1,2-a]indol-10-ones.