Difluoromethylation of heterocyclesviaa radical process

Abstract

Difluoromethylation is of prime importance for its applicability in functionalizing diverse fluorine-containing heterocycles, which are core moieties of various biologically and pharmacologically active ingredients. Due to their significant biological and...

Visible-Light Photoredox-Catalyzed Three-Component Reaction of Carbazoles with Alkenes and S-(Difluoromethyl)sulfonium Salt: A Practical Approach to Access Difluoroalkyl-Functionalized Carbazoles

“…Difluoromethyl (CF 2 H) is a unique moiety bearing fluorine, which is considered as an ideal bioisostere of alcohol, thiol, or amine groups with improved metabolic stability and acts as a more lipophilic hydrogen bond donor, , thus facilitating the parent molecule’s fantastic changes in chemical, physical, and biological properties. , Therefore, CF 2 H-containing compounds have received considerable interest in pharmaceuticals, agrochemicals, and materials, − and the construction of difluoromethyl-functionalized molecules has attracted great attention in recent years. Consequently, numerous methods have been reported for the preparation of CF 2 H-substituted compounds . On the other hand, carbazole represents an important type of nitrogen-containing heterocyclic compounds because of their distinct various functions, properties, and biological activities endowed by their intriguing structural features, with potential applications in photoelectrical materials, dyes, pharmaceuticals, and supramolecular recognition (ion recognition) .…”

Recent advances in trifluoroethylation reaction

“…1–3 This is due to the unique stereoelectronic effect of fluorine, as it can have profound effects on its chemical and bioactive properties such as lipophilicity, metabolic stability, membrane permeability, and bioavailability. 4,5 Among the various fluorine-containing functional groups, 6 2,2,2-trifluoroethyl (CF 3 CH 2 ), considered as the bioisostere of ethyl or ethoxy group, is attracting increasing attention from synthetic chemists due to its potential applications in medicinal chemistry and related fields. 7–9 However, compared to the substantial progress made in trifluoromethylation methods, 10–12 the assembly of trifluoroethyl entity into various molecules still lags behind.…”