A Copper-Catalyzed Synthesis of 3-Aroylindoles via a sp3 C-H Bond Activation Followed by C-C and C-O Bond Formation
Anupal Gogoi, Srimanta Guin, Saroj Kumar Rout and Bhisma K. Patel*
*Department of Chemistry, Indian Institute of Technology, Guwahati, Guwahati 781039, India, Email: pateliitg.ernet.in
A. Gogoi, S. Guin, S. K. Rout, B. K. Patel, Org. Lett., 2013, 15, 1802-1805.
DOI: 10.1021/ol400692b (free Supporting Information)
Cu-catalyzed sp3 C-H bond activation α to the nitrogen atom of o-alkynylated N,N-dimethylamines followed by an intramolecular nucleophilic attack with the alkyne, using an aqueous solution of tert-butyl hydroperoxide (TBHP) as the oxidant, enables a tandem catalytic synthesis of 3-aroylindoles. In this synthesis, both C-C and C-O bonds are installed at the expense of two sp3 C-H bond cleavages.
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