title: Mechanistic insights on iodine(III) promoted metal-free dual C-H activation involved in the formation of a spirocyclic bis-oxindole.
abstract: The mechanism of a metal-free, phenyliodine(III) bis(trifluoroacetate) promoted, dual aryl C-H activation of an anilide to a spirocyclic bis-oxindole is examined using density functional theory (M06-2X). The most preferred pathway proceeds through the involvement of a novel iodonium ion intermediate and a pivotal trifluoroacetate counterion. The two sequential aryl C-H activations, assisted by trifluoroacetate as well as the superior leaving group ability of PhI, facilitate the formation of spirocyclic bis-oxindole.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
authors.forename: A
authors.initials: A
authors.lastname: Sreenithya
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
authors.forename: Raghavan B
authors.initials: RB
authors.lastname: Sunoj