title: Regiocontrolled synthesis of carbocycle-fused indoles via arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride.
abstract: [formula: see text] A new, regiocontrolled synthesis of carbocycle-fused indoles has been developed. The two-step procedure involves first the regiospecific arylation of silyl enol ethers with o-nitrophenylphenyliodonium fluoride (1). Reduction of the nitro group on the aromatic ring with TiCl3 followed by spontaneous condensation of the aniline with the ketone then affords the indole products.
authors.affiliation: Department of Chemistry, University of Chicago, Illinois 60637, USA.
authors.forename: T
authors.initials: T
authors.lastname: Iwama
authors.forename: V B
authors.initials: VB
authors.lastname: Birman
authors.forename: S A
authors.initials: SA
authors.lastname: Kozmin
authors.forename: V H
authors.initials: VH
authors.lastname: Rawal
mesh_terms: D007211:Indoles / Q000138:chemical synthesis*; D007462:Iodobenzenes / Q000138:chemical synthesis* / Q000737:chemistry; D009578:Nitrobenzenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007211:Indoles; D007462:Iodobenzenes; D009578:Nitrobenzenes; C410466:2-nitrophenylphenyliodonium