Ru(II)-Catalyzed Direct C(sp²)–H Activation/Selenylation of Arenes with Selenyl Chlorides

Abstract

A new ruthenium catalytic system was developed for the construction of a C(sp(2))-Se bond with the assistance of directing groups. This protocol features mild reaction conditions, wider substrate scope, and convenient late-stage selenylation of bioactive molecules.

A comprehensive overview of directing groups applied in metal-catalysed C–H functionalisation chemistry

“…Regarding C–heteroatom bond formation, selenation with phenylselenyl chloride was reported by Zhang ( Scheme 153J ), 938 and halogenation by Wang and Hierso. Wang used Na halides and Rh catalysis for iodination, bromination and chlorination of a few 1-phenyl-1 H -pyrazoles ( Scheme 153K ), 772 while fluorination could be achieved using NFSI with Pd catalysis, as reported by Hierso ( Scheme 153L ).…”

Recent Advances in C–H Bond Functionalization with Ruthenium-Based Catalysts

“…Recently, ruthenium-catalysed C-H bond functionalization has been studied in various reactions, namely arylation [15], alkenylation [16], and annulation [26]. Subsequently, several new reactions have been discovered, such as direct C-H bond oxygenation [32], amidation [33], amination [34], cyanation [35], halogenations [36] and selenylation [37]. These reactions on ruthenium-catalysed C-H bond functionalization have been presented in numerous research papers and review articles by several groups [15,16,25,26,[38][39][40].…”

Ligand‐Free Palladium(II)‐Catalyzed ortho‐C–H Chalcogenations of N‐Arylsulfonamide via Weak Coordination

“…The transition metal catalyzed direct chalcogenation of inert aryl C–H bonds is one of the most efficient methods of constructing unsymmetrical diarylselenide and diarylsulfide skeletons . In recent years, many wonderful achievements about chelation‐assisted regioselective C–H chalcogenation of arenes have been made by Ackermann, Baidya, Zhang, Li, Yang et al Most of these processes are accomplished through the strong coordination of N ‐containing directing groups such as pyrimidine, pyridine, oxime, N ‐oxide or bidentate directing groups . Nevertheless, the directing groups with weak coordination have been rarely reported.…”