Single-electron transfer oxidation-induced C–H bond functionalization via photo-/electrochemistry

Abstract

Single-electron transfer (SET) oxidation-induced C–H bond functionalization usually proceeds smoothly under mild conditions due to the assistance of an oxidant, light, or electricity. SET oxidation-induced C–H bond functionalization can be rationally designed according to the oxidation potential of substrates and the interaction between oxidation tools and substrates. SET oxidation-induced C–H functionalization activates the whole molecule rather than a certain C–H bond, leading to special site selectivity. The development of SET oxidation-induced C–H bond functionalization generates more promising oxidation modes such as photoelectrochemistry to achieve more difficult reactions. C–H bond functionalization, which meets with the concept of atom and step economy, has been the hot topic in synthetic chemistry during the past decade. The most representative transition metal-catalyzed C–H bond functionalization usually involves the cleavage of a C–H bond, formation of a C–M bond, and subsequent transformation. Recently, with the fast development of oxidation modes (photo-, electrochemistry), single-electron transfer (SET) oxidation-induced C–H bond functionalization has attracted more and more attention. The substrate molecule is initially oxidized to form radical cation species by losing an electron. Then, the active radical cation can be further functionalized more easily. The feature of SET oxidation-induced C–H bond functionalization provides more opportunities for constructing compounds under mild conditions. C–H bond functionalization, which meets with the concept of atom and step economy, has been the hot topic in synthetic chemistry during the past decade. The most representative transition metal-catalyzed C–H bond functionalization usually involves the cleavage of a C–H bond, formation of a C–M bond, and subsequent transformation. Recently, with the fast development of oxidation modes (photo-, electrochemistry), single-electron transfer (SET) oxidation-induced C–H bond functionalization has attracted more and more attention. The substrate molecule is initially oxidized to form radical cation species by losing an electron. Then, the active radical cation can be further functionalized more easily. The feature of SET oxidation-induced C–H bond functionalization provides more opportunities for constructing compounds under mild conditions.