title: Iodine(V) reagents in organic synthesis. Part 3. New routes to heterocyclic compounds via o-iodoxybenzoic acid-mediated cyclizations: generality, scope, and mechanism.
abstract: The discovery and development of the o-iodoxybenzoic acid (IBX) reaction with certain unsaturated N-aryl amides (anilides) to form heterocycles are described. The application of the method to the synthesis of delta-lactams, cyclic urethanes, hydroxy amines, and amino sugars among other important building blocks and intermediates is detailed. In addition to the generality and scope of this cyclization reaction, this article describes a number of mechanistic investigations suggesting a single electron transfer from the anilide functionality to IBX and implicating a radical-based mechanism for the reaction.
authors.affiliation: Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
authors.forename: K C
authors.initials: KC
authors.lastname: Nicolaou
authors.forename: P S
authors.initials: PS
authors.lastname: Baran
authors.forename: Y-L
authors.initials: YL
authors.lastname: Zhong
authors.forename: S
authors.initials: S
authors.lastname: Barluenga
authors.forename: K W
authors.initials: KW
authors.lastname: Hunt
authors.forename: R
authors.initials: R
authors.lastname: Kranich
authors.forename: J A
authors.initials: JA
authors.lastname: Vega
mesh_terms: D000588:Amines / Q000138:chemical synthesis; D000606:Amino Sugars / Q000138:chemical synthesis; D000813:Anilides / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007462:Iodobenzenes; D007463:Iodobenzoates / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis; D014520:Urethane / Q000138:chemical synthesis
chemical_list: D000588:Amines; D000606:Amino Sugars; D000813:Anilides; D006571:Heterocyclic Compounds; D007462:Iodobenzenes; D007463:Iodobenzoates; D007769:Lactams; D014520:Urethane; C476101:o-iodoxybenzoic acid