Hypervalent Iodine‐Mediated Selective Oxidative Functionalization of (Thio)chromones with Alkanes

CC bond formation is the most fundamental way for the chain propagation in organic molecules. This achievement through tandem oxidation of two different CH bonds represents the state of the art in organic synthesis. Selective functionalization of the ubiquitous aliphatic CH 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 CH 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.