The cumene/O₂ system: a very simple tool for the radical chain oxidation of some functional groups

Abstract

Just boil it in cumene! A general metal-free oxidation method is described.

Study on the cleavage of alkyl-O-aryl bonds by in situ generated hydroxyl radicals on an ORR cathode

“…This is very similar to the process of industrial production of phenol and acetone by cumene process, in which ROS was used for oxidizing cumene to form cumene radicals, and obtained a phenolic hydroxyl group on the benzene ring. 35 In view of this, similar methods can be used in the depolymerization of lignin to introduce phenolic hydroxyl groups on the benzene ring and further utilize the introduced phenolic hydroxyl groups to form active sites, trigger the chain-break of the linkages among the structural units, and achieve the nal depolymerization of lignin.…”

Bridging Plastic Recycling and Organic Catalysis: Photocatalytic Deconstruction of Polystyrene via a C–H Oxidation Pathway

“…Overall, this process can break two C–H bonds of a secondary sp 3 carbon (−CH 2 −) and form a carbonyl (CO) group. Reports on thermal C–H oxidation of a tertiary sp 3 carbon (only one hydrogen on the carbon) that can break the adjacent C–C bond (instead of a C–H bond) are available, but the process is not catalytic and requires high temperatures (150–200 °C). Recent reports also show that polyolefins (e.g., PE and PP) can be modified by C–H functionalization to form functionalized polymers containing oxygenated groups, − indicating that polymer reactions can be performed and studied in a way similar to that of small molecules.…”

Emerging unconventional organic solvents for C–H bond and related functionalization reactions

“…Cumene however, has been demonstrated by some of us to accommodate this very same ultra-simple reaction at only 1 bar of dioxygen gas, under otherwise similar reaction conditions (Method B). 38 This effect is what Maes 39 recently described as the ''Mukaiyama trick.'' 40 Its principle, which Mukaiyama did not exemplify on cumene but rather on other components, relies on the ability of cumene to readily activate dioxygen towards the cumyl radical and other activated species such as the cumyl hydroperoxide.…”