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

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Abstract

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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Key Words

indoles, tert-butyl hydroperoxide

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ID: J54-Y2013