Copper-Catalyzed Oxidative C(sp3)-H/C(sp3)-H Cross-Coupling Reaction of 3-Methylbenzo[c]isoxazoles with Methyl Ketones: Access to Indigoid Analogues.

A copper-catalyzed oxidative C(sp3)-H/C(sp3)-H cross-coupling reaction of methyl ketones and 3-methylbenzo[c]isoxazoles has been developed for the direct synthesis of 3-oxoindolin-2-ylidene derivatives. This process involves an intermolecular nucleophilic addition/ring-opening/aza-Michael addition cascade, providing indigoid analogues with high atom economy and as single isomers exclusively under mild conditions.