title: Hypervalent iodine-mediated selective oxidative functionalization of (thio)chromones with alkanes.
abstract: C-C bond formation is the most fundamental way for the chain propagation in organic molecules. This achievement through tandem oxidation of two different C-H bonds represents the state of the art in organic synthesis. Selective functionalization of the ubiquitous aliphatic C-H bonds offers an attractive option for this oxidative cross-coupling methodology. To develop such a methodology under mild and "metal-free" conditions remains challenging. Herein, we report hypervalent iodine-mediated selective oxidative functionalization of aliphatic C-H bonds of alkanes with chromones and (thio)chromones. A wide range of alkanes, both cyclic and acyclic, has been found to react selectively and predictably in good yields. The developed methodology is also the first report of a direct oxidative functionalization of the C-2 position of (thio)chromones with alkanes to access bioactive compounds.
authors.affiliation: Max Planck Institute für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany), Fax: (+49) 231-133-2499.
authors.forename: Rishikesh
authors.initials: R
authors.lastname: Narayan
authors.forename: Andrey P
authors.initials: AP
authors.lastname: Antonchick
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002867:Chromones / Q000138:chemical synthesis / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D000473:Alkanes; D002867:Chromones; D002244:Carbon; D007455:Iodine
keywords: CH activation; chromones; iodine; metal-free conditions; oxidative coupling