Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles

Abstract

With [Ru(p-cymene)Cl₂]₂ as catalyst, diazo-β-ketoanilides would undergo intramolecular carbenoid arene C–H bond functionalization to afford 3-alkylideneoxindoles in up to 92% yields. The reaction occurs under mild conditions and exhibits excellent chemoselectivity. The lack of primary KIE (k_H/k_D ∼ 1) suggests that the reaction should not proceed by rate-limiting C–H bond cleavage; a mechanism involving cyclopropanation of the arene is proposed.