Recent progress in the oxidative bromination of arenes and heteroarenes

Abstract

Oxidative bromination has been serving as a powerful tool for the synthesis of bromo-containing molecules, as this bromination strategy features environmental friendliness, high flexibility in reaction system design and wide...

Mono and Dinuclear Palladium Pincer Complexes of NNSe Ligand as a Catalyst for Decarboxylative Direct C−H Heteroarylation of (Hetero)arenes

“…The heteroarenes molecules are a privileged class of molecules with a diverse range of applications in polymer industries, [37] semiconductor industries, [38] natural products, [39] drug molecules, [40] and optoelectronic applications [41] . The key challenge in constructing the heteroarenes molecules is the homocoupling reaction between both the starting materials which reduces the yield of heterocoupling products [42] …”

Recent advances in oxidative chlorination

“…14 Compared with bromination, 15 good selectivity is a little more difficult to achieve as the active species in chlorination is more reactive than that in bromination. Furthermore, oxidative chlorination 16 should be more difficult to control than oxidative bromination, since chloride is harder to oxidize to chlorinating agent than bromide because of the difference of oxidation potentials. A chlorinating reagent-focused review has been disclosed by Luca and coworkers on the utilization of TCCA in chlorination reactions.…”

Electrochemical C–H Mono-/Multi-Bromination Regulation of N-Sulfonylanilines on a Cost-Effective Carbon Fiber Electrode and Its Prospective Electroactive Molecule Screening

“…As a common organic building block for diverse transformations, aryl bromides are widely applied in coupling reactions , and also are usually found in natural products and bioactive compounds. , Among them, brominated anilines are of significance for clinical drugs, such as bromazepam (antianxiety), binimetinib (BRAF/MEK inhibitor), vandetanib (antithyroid cancer), and bromhexine (expectorant) (Figure a). In this regard, various synthesis methods for bromination of anilines have been developed, of which the direct bromination through specific brominating reagents or oxidants via an electrophilic aromatic substitution is the popular one and widely used. − The past decade has witnessed that the electrochemical organic synthesis has become one of the fascinating fields owing to its redox ability without using chemical oxidants. − Recently, we noted that the direct electrochemical C–H bromination of anilines could be accomplished under oxidant-free conditions from simple and available bromine sources, such as the bromine anions (NaBr, NH 4 Br, and n -Bu 4 NBr) and brominated alkanes (CH 2 Br 2 , 3-bromopropyne, and 2-bromoethan-1-ol) (Figure b). Despite these significant advances, there are some limitations: (1) the relatively expensive electrodes were required, such as Pt or RVC, and (2) the substrate scope was limited to the unique 8-aminoquinolines, , N , N- dialkylanilines, ,, N -acylated anilines, and free anilines .…”