4-Cyclopentene-1,3-dione (930-60-9) 's Synthetic route

Photochemical Activation of a Hydroxyquinone-Derived Phenyliodonium Ylide by Visible Light: Synthetic and Mechanistic Investigations

Jalali, Mona  Ho, Curtis C.  Fuller, Rebecca O.  Lucas, Nigel T.  Ariafard, Alireza  Bissember, Alex C.

We have identified and extensively investigated the photochemical activation and reaction of a hydroxyquinone-derived phenyliodonium ylide in the presence of visible light using experiment and theory. These studies revealed that in its photoexcited state this iodonium is capable of facilitating a range of single-electron transfer (SET) processes, including hydrogen atom transfer (HAT), a Povarov-type reaction, and atom-transfer radical addition chemistry. Where possible, we have employed density functional theory (DFT) to develop a more complete understanding of these photoinduced synthetic transformations.