title: Ruthenium-catalyzed intramolecular cyclization of diazo-β-ketoanilides for the synthesis of 3-alkylideneoxindoles.
abstract: With [Ru(p-cymene)Cl(2)](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.
authors.affiliation: State Key Laboratory for Chirosciences, Department of Applied Biology and Chemical Technology, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong.
authors.forename: Wai-Wing
authors.initials: WW
authors.lastname: Chan
authors.forename: Tsz-Lung
authors.initials: TL
authors.lastname: Kwong
authors.forename: Wing-Yiu
authors.initials: WY
authors.lastname: Yu
mesh_terms: D000813:Anilides / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry*
chemical_list: D000813:Anilides; D001391:Azo Compounds; D007211:Indoles; D009942:Organometallic Compounds; D012428:Ruthenium