Application of DMSO as a methylthiolating reagent in organic synthesis

Abstract

In the past decades, DMSO has been widely used not only as a common solvent, but also as an environmentally benign oxidant in various organic transformations. Most strikingly, DMSO can...

I2/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis

“…Furthermore, it also functions as a terminal oxidant, eliminating the need for transition metals. 21 Fascinatingly, the combination of these two readily accessible and benign molecules presents new avenues for simple, inexpensive, facile, eco-friendly, metal-free, and atom-economical reaction strategies, facilitating simple oxidation to chemoselective and regioselective oxidation, sulfenylation, and amination to effectively generate C-C, C-X, C-O, C-S, S-N and C-N bonds, affording various bioactive, pharmaceutical, industrial, and applied molecular structures. [22][23][24][25][26] This review presents a detailed summary of the research advancements achieved in the I 2 /DMSO catalytic system for the formation of C-C and C-heteroatom bonds from 2018 to now.…”

Electrochemical C3-methylthiolation of imidazopyridines with dimethyl sulfoxide

“…The application of DMSO as a methylthiolating reagent in the functionalization of heterocycles has received much attention in recent years. 9 In these methylthiolation reactions, a promoter was generally needed. In 2013, Roychowdhury et al 10 developed a methylthiolation reaction of imidazofused heterocycles, in which POCl 3 was used as the activator and an electrophilic chlorodimethylsulfonium salt was believed to be a key intermediate.…”

Iodine(iii)-mediated dehydroaromatization of cyclohexanones with primary amines and CD3SSO3Na to access ortho-SCD3 anilines

“…8 Although elegant, it has drawbacks, such as the use of an acyl halide to activate dimethyl sulfoxide, causing poor tolerance of acid sensitive functional groups; furthermore, the need for solvent quantities of expensive d 6 -DMSO inhibits the widespread application of such methods in industry. 9 Recently, an electrophilic reagent, PhSO 2 SCD 3 , has been developed and is used for the two-component trideuteromethylthiolation of arylboronic acid, aryldiazonium salts and aryl (hetero) iodides. 10 However, owing to the electrophilic nature of the trideuteromethylthiolation reagent, substantial N -SCD 3 formation was observed.…”