A continuous flow bromodimethylsulfonium bromide generator: application to the synthesis of 2-arylaziridines from styrenes

Investigation of Parameter Control for Electrocatalytic Semihydrogenation in a Proton-Exchange Membrane Reactor Utilizing Bayesian Optimization

“…The PEM reactor features many characteristics designed to overcome the disadvantages of conventional electrosynthetic processes, such as the necessity of supporting electrolytes. Moreover, because the PEM reactor is a flow reactor (Masui et al, 2019;Ashikari et al, 2020;Colella et al, 2020;Harenberg et al, 2020;Ichinari et al, 2020;Otake et al, 2020;Saito and Kobayashi, 2020;Watanabe et al, 2020;Ahn et al, 2021;Prieschl et al, 2021;Sivo et al, 2021), it offers numerous advantages, including precise control of the reaction time, the applicability of successive reactions, and scalability, which are rarely applicable in batch electrosynthesis (Elsherbini and Wirth, 2019;Noël et al, 2019;Hu et al, 2020). Therefore, various applications of PEM reactor systems utilizing electrosynthetic processes, such as the reduction of toluenes (Takano et al, 2016;Fukazawa et al, 2018) and alkenes (Ogumi et al, 1981), and asymmetric hydrogenation of α,β-unsaturated acids (Fukazawa et al, 2020), have been reported (Raoult et al, 1984;Jorissen, 1996;Kishi et al, 2020;Fukazawa et al, 2021).…”

Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

“…Adapted with permission from Ref. [136]; Copyright (2020) Wiley. obtained a conversion of 99.4 %, resulting in an isolated yield of 82.5 %.…”

“…Several styrene and amine derivatives were also successfully reacted with yields ranging from 26 to 62 %. [136] Yu and co-workers focussed on the upscaling of the reaction. They brominated 3-methylanisole with the HBr/DMSO-couple, using DMSO and water as solvent.…”

“…Recently, Prieschl et al . utilised the superior mixing and heat transfer of microreactors to improve the oxidative bromination with BDMSB 44 , e. g. by safely removing the heat generated by the exothermic formation of BDMSB 44 [136] . They also found that using HBr in AcOH instead of the regular commercial HBr in H 2 O solution, and scavenging the formed water in the formation of BDMSB 44 with acetic anhydride increased the formation of BDMSB 44 , and thus the reaction rate.…”

The Role of (BDMS) Bromodimethylsulfonium bromide as a Catalyst and Brominating Reagent: A Concise Overview

“…An uninterrupted flow route was developed by Michael et al from eagerly accessible and quite harmless DMSO and HBr as preliminary materials for the preparation of aziridines by alkenes based on the in situ creation of bromodimethylsulfonium bromide (BDMS) (Scheme 25). [34] In this route, BDMS was formed from hydrogen bromide and dimethylsulfoxide in the presence of the olefin, resulting the corresponding 1,2-bromodimethylsulfonium bromide addition product. Remarkably, the exothermic formation of BDMS could be eagerly controlled in flow mode at room temperature, rendering a safe and reliable process.…”