Journal
JOURNAL OF FLOW CHEMISTRY
Volume 11, Issue 2, Pages 117-125Publisher
SPRINGER
DOI: 10.1007/s41981-020-00125-2
Keywords
Bromodimethylsulfonium bromide; Continuous flow; Chemical generators; Aziridines
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Funding
- CC FLOW project (Austrian Research Promotion Agency FFG) through the Austrian COMET Program by the Austrian Federal Ministry of Transport, Innovation, and Technology (BMVIT) [862766]
- Austrian Federal Ministry of Science, Research and Economy (BMWFW)
- State of Styria (Styrian Funding Agency SFG)
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The method utilizes BDMS for the synthesis of aziridines, offering an efficient and rapid process that can control the exothermic reaction at room temperature, ensuring safety and reliability.
A continuous flow procedure for the synthesis of aziridines from alkenes based on the in situ generation and utilization of bromodimethylsulfonium bromide (BDMS) is presented. In this process, BDMS was generated from hydrogen bromide and dimethylsulfoxide in the presence of the olefin, ensuing the corresponding 1,2-bromodimethylsulfonium bromide addition product. The solution containing this intermediate was mixed with a primary amine in flow, resulting in a rapid aziridination in a fast 3-step telescoped process. Notably, the exothermic formation of BDMS could be readily controlled in flow mode at room temperature, rendering a safe and reliable process. The complete sequence only required 7 min of total residence time, and provided a variety of 2-aryl aziridines in synthetically useful yields.
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