Oxidative C–S bond cleavage reaction of DMSO for C–N and C–C bond formation: new Mannich-type reaction for β-amino ketones

Abstract

A novel oxidative C-S bond cleavage reaction of DMSO for N-methylation course and subsequent C-C bond formation is described. A series of aryl ketones as well as acetone derivatives could be selectively converted into the 10

Convenient Preparation of N-Acylbenzoxazines from Phenols, Nitriles, and DMSO Initiated by a Catalytic Amount of (COCl)2

“…The fact that DMSO acts as a methylene synthon can be dated back to Traynelis and Hergenrother’s work in 1964, in which formaldehyde from the decomposition of DMSO upon prolonged reflux reacted with diols to form cyclic acetals or with amides to form methylenebisamides . Many milder methods of transferring a methylene unit from DMSO have been developed recently, such as using DMSO with oxidants, transition-metal catalysts, or other activating agents . The method in this present work provides an alternative approach to utilizing DMSO as a source of methylene synthon, which is easily operated and cost-efficient since only a catalytic amount of (COCl) 2 is needed.…”

The Role of Sulphonamides and N‐Sulphonyl Ketimines/Aldimines as Directing Groups in the Field of C−H Activation

“…There are many documented synthetic reactions for the synthesis of this class of compounds but C−H activation approach has garnered attention of researchers due to its practicality, environmental sustainability and atom economy (Figure 2). [57–60] …”

The Applications of Dimethyl Sulfoxide as Reagent in Organic Synthesis

“…In 2015, the research groups of Liu,13 Wang14 and their co‐workers independently reported a novel oxidative CS bond cleavage reaction of DMSO for dual CC and CN bond formation. The authors have shown that various acetylarenes and heteroarenes could be selectively converted into the corresponding β‐amino ketones (Scheme ), which are commonly found in biologically active compounds and pharmaceuticals.…”