Copper(I)-catalyzed tandem reaction of 2-iodophenols with isothiocyanates in room temperature ionic liquids

Influence of Substituents in the Aromatic Ring on the Strength of Halogen Bonding in Iodobenzene Derivatives

“…The studied compounds also have many practical applications. Halogenated derivatives of benzoic acids, anilines, and phenols can be found in various biological applications, − pharmaceuticals, biochemistry, − electrochemistry, catalysis, − etc. − Therefore, the investigation of the XB behavior of these types of molecules may also shed light on the details of these processes.…”

Synthesis of 2-Arylimino-6,7-dihydrobenzo[d][1,3]oxathiol-4(5H)-ones via Rh2(OAc)4-Catalyzed Reactions of Cyclic 2-Diazo-1,3-diketones with Aryl Isothiocyanates

“…53,54 The importance of 2-iminobenzo-1,3-oxathioles has stimulated the development of efficient methods for their synthesis. 55−58 However, there are still few approaches for their synthesis including a copper-catalyzed tandem reaction of ortho -iodophenols and isothiocyanates, 59−61 a rhodium(II)-catalyzed reaction of α-diazocarbonyl compounds with isothiocyanates, 56 Rh(II)-catalyzed denitrogenative reactions of 1-sulfonyl-1,2,3-triazoles with isothiocyanates, 58 and [4 + 1] cycloaddition of ortho -thioquinones with isocyanides. 54 These available synthetic approaches generally suffer from narrowed substrate scopes, the requirement of organoligands, and relatively low efficiencies associated with the tedious multistep manipulation, which has limited their further applications.…”

“…As a privileged fragment, the benzo-1,3-oxathiole core is a ubiquitous subunit in a variety of important heterocyclic compounds with remarkable pharmaceutical or biochemical activities. − Among them, 2-iminobenzo-1,3-oxathioles are an important class of benzo-1,3-oxathiole derivatives for the potential pharmaceutical or biochemical activities of their derivatives. , The importance of 2-iminobenzo-1,3-oxathioles has stimulated the development of efficient methods for their synthesis. − However, there are still few approaches for their synthesis including a copper-catalyzed tandem reaction of ortho -iodophenols and isothiocyanates, − a rhodium­(II)-catalyzed reaction of α-diazocarbonyl compounds with isothiocyanates, Rh­(II)-catalyzed denitrogenative reactions of 1-sulfonyl-1,2,3-triazoles with isothiocyanates, and [4 + 1] cycloaddition of ortho -thioquinones with isocyanides . These available synthetic approaches generally suffer from narrowed substrate scopes, the requirement of organoligands, and relatively low efficiencies associated with the tedious multistep manipulation, which has limited their further applications.…”

Copper/N,N,N′,N′‐Tetramethylethylenediamine‐Catalyzed Synthesis of N‐Substituted Benzoheterocycles via CS Cross‐ Coupling at Ambient Temperature in Water

“…Cai et al. also reported a copper‐catalyzed approach to synthesize 2‐imino‐1,3‐oxathioles in ionic liquids 9c. Despite these interesting works, developing an environmentally friendly process to synthesize N‐substituted benzoheterocycles at ambient temperature in water is still meaningful.…”