A Copper-Catalyzed Synthesis of 3‑Aroylindoles via a sp3 C–H Bond Activation Followed by C–C and C–O Bond Formation
journal contributionposted on 19.04.2013 by Anupal Gogoi, Srimanta Guin, Saroj Kumar Rout, Bhisma K. Patel
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An efficient Cu(I)-catalyzed synthesis of 3-aroylindoles has been achieved from o-alkynylated N,N-dimethylamines via a sp3 C–H bond activation α to the nitrogen atom followed by an intramolecular nucleophilic attack with the alkyne using an aqueous solution of tert-butyl hydroperoxide (TBHP) as the oxidant. In this tandem catalytic synthesis of 3-aroylindoles both C–C and C–O bonds are installed at the expense of two sp3 C–H bond cleavages.