title: 1,2-Halogen migration in haloallenyl ketones: regiodivergent synthesis of halofurans.
abstract: Selective 1,2-iodine, bromine, and chlorine migration in haloallenyl ketones in the presence of Au catalyst has been demonstrated. It was found that, depending on the nature of the Au catalyst used, either selective bromine migration or hydrogen shift occurs, leading to the formation of 3- or 2-bromofurans, respectively. Halirenium intermediate was proposed for the unusual 1,2-halogen migration. This cascade transformation allows for mild and efficient synthesis of various types of 3-halofurans.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
authors.forename: Anna W
authors.initials: AW
authors.lastname: Sromek
authors.forename: Marina
authors.initials: M
authors.lastname: Rubina
authors.forename: Vladimir
authors.initials: V
authors.lastname: Gevorgyan
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*
chemical_list: D000466:Alkadienes; D005663:Furans; D006846:Hydrocarbons, Halogenated; D007659:Ketones; C025947:propadiene