Aerobic Catalytic Features in Photoredox- and Copper-Catalyzed Iodolactonization Reactions.

Abstract

Mechanistic evaluations and comparison of two important aerobic catalytic oxidation processes, aerobic copper catalysis and photoredox catalysis, are performed. Interesting and distinct catalytic behaviors were observed for a common reaction of iodolactonization of alkenoic acids. Namely, the aerobic copper catalysis requires the formation of a copper carboxylate, whereas the aerobic photoredox catalysis requires the addition of proton sources to proceed to completion. Furthermore, the iodolactone products obtained from these catalytic processes are extensively derivatized to a number of functionalized lactones, including aryl lactones generated from the nickel-catalyzed reductive coupling with aryl halides.