title: Phenyliodine bis(trifluoroacetate)-mediated oxidative C-C bond formation: synthesis of 3-hydroxy-2-oxindoles and spirooxindoles from anilides.
abstract: The reaction of phenyliodine bis(trifluoroacetate) (PIFA) with a series of anilides 1 (E = CO(2)Et) in CF(3)CH(2)OH was found to give 3-hydroxy-2-oxindole derivatives 2, while that with various anilides 1' (E = CON(R(4))Ar) afforded the C(2)-symmetric or unsymmetric spirooxindoles 3. These processes feature a metal-free oxidative C(sp(2))-C(sp(3)) bond formation, followed by oxidative hydroxylation or spirocyclization.
authors.affiliation: Tianjin Key Laboratory for Modern Drug Delivery & High-Efficiency, School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China.
authors.forename: Junwei
authors.initials: J
authors.lastname: Wang
authors.forename: Yucheng
authors.initials: Y
authors.lastname: Yuan
authors.forename: Rui
authors.initials: R
authors.lastname: Xiong
authors.forename: Daisy
authors.initials: D
authors.lastname: Zhang-Negrerie
authors.forename: Yunfei
authors.initials: Y
authors.lastname: Du
authors.forename: Kang
authors.initials: K
authors.lastname: Zhao
mesh_terms: D000813:Anilides / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D005463:Fluoroacetates; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000078183:Oxindoles; D014269:Trifluoroacetic Acid / Q000737:chemistry*
chemical_list: D000813:Anilides; D005463:Fluoroacetates; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D014269:Trifluoroacetic Acid