Photoredox-Catalyzed Generation of Acetonyl Radical in Flow: Theoretical Investigation and Synthetic Applications

A hydrogen atom transfer (HAT) step from acetone allowed the smooth generation of acetonyl radical that was then exploited as synthon in the mild formation of C-C bonds under flow conditions. The process was promoted by aryl radicals photocatalytically generated via single-electron transfer (SET) reduction of arenediazonium salts. The mechanism has been investigated by a combined experimental and computational approach and further supported by deuterium labeling experiments.