Pan, LeiElmasry, JosephOsccorima, TomasCooke, Maria VictoriaLaulhé, Sébastien2023-09-252023-09-252021Pan L, Elmasry J, Osccorima T, Cooke MV, Laulhé S. Photochemical Regioselective C(sp3)-H Amination of Amides Using N-Haloimides. Org Lett. 2021;23(9):3389-3393. doi:10.1021/acs.orglett.1c00831https://hdl.handle.net/1805/35736A metal-free regioselective C(sp3)-H amination of amides using N-haloimides in the presence of lithium tert-butoxide and visible light is presented herein. This photoexcited approach is straightforward, and it aminates a wide variety of amides under mild conditions without the use of photocatalysts, external radical initiators, or oxidants. A halogen-bonded intermediate between the tert-butoxide base and the N-haloimide is proposed to be responsible for the increased photoreactivity. Calculations show that the formation of this electron donor-acceptor complex presents an exergonic energy profile.en-USPublisher PolicyAmidesAminationMolecular structureOxidantsArticle