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Nickel-Catalyzed trans-Carboamination across Internal Alkynes to Access Multifunctionalized Indoles

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journal contribution
posted on 26.10.2020, 18:08 by Shrikant D. Tambe, Naeem Iqbal, Eun Jin Cho
A Ni-catalyzed reaction was developed for the synthesis of multifunctionalized indoles. The reaction proceeded through oxidative cyclization of the Ni(0)/P^N complex with an enyne system, 2-alkynyl anilinoacrylate, to provide a nickelacycle intermediate. The trans-carboamination around the internal alkyne was achieved by syn/anti-rotation of the Ni-carbenoid intermediate formed by C–N bond cleavage of the nickelacycle, and 3-alkenylated indoles were formed by C–N bond-forming reductive elimination. Notably, the synthesized indoles could be successfully transformed to functionalized carbazoles.