Photocatalytic Incorporation of an Oxime Ether Functional Group at Inert C(sp³)–H Bonds via HAT

Abstract

Herein, we describe a photocatalytic method for the direct incorporation of an oxime functional group at inert C(sp 3 )− H bonds of ethers, amides, alcohols, amines, and alkanes via HAT with photoexcited eosin Y under mild conditions using air and a blue LED. Many useful functional groups are tolerated in this process, and the reaction is scalable. A series of mechanistic studies were carried out to support the radical pathway proposed for the process.

Photo/Electrochemical‐Mediated C(sp3)−H Bond Functionalization of (Thio)Ethers

“…Oxime functional groups are present in many bioactive compounds and act as precursors for many important functional groups. In 2022, Guin's group reported the photocatalytic C(sp 3 )−H oxime ether functionalization reaction of inert ethers, amides, alcohols, and amines as well as alkanes (Scheme 26a) [35] . The reaction is carried out using inexpensive Na 2 −eosin Y (Na 2 −EY) as the catalyst, air as the only oxidant, and blue LEDs as the energy source, and has the advantages of good functional group tolerance and scalability.…”