Our paper entitled "Design of Trifluoroalkenyliodonium salts for Hypervalency Aided Alkenylation‐Cyclization Strategy: Metal‐free Construction of Aziridine Ring" was highlighted by OPR&D! The highlights are selected by a group of industrial chemists as a service to the readership who has a strong interest in practical chemistry that addresses and solves industrial questions.
The efficient construction of small heterocyclic fluorinated building blocks continues to be a major topic of interest for the synthetic community. Novák and co-workers at Eötvös University in Budapest described a new methodology for the synthesis of trifluoromethylated aziridines that expands for the first time the scope of substrates to nonaromatic amines ( Angew. Chem., Int. Ed. 2018, 57, 6643). For that purpose, the authors designed and synthesized trifluoropropenyl iodonium salts as new C2–CF3 synthons. Under the best conditions, dichloromethane as the solvent with 2 equiv of sodium carbonate as the base, an array of substituted alkylamines as well as (hetero)arylamines were converted into trifluoromethylated aziridines in moderate to high yields. An impressive number of functional groups, including alcohols and unprotected anilines, are well-tolerated. DFT calculations were performed to provide insight into the mechanism of the reaction.
Wenyi Zhao, Sylvain Guizzetti, James A. Schwindeman, David S. B. Daniels, Carlos A. Guerrero, David Philip Day, John Knight, Org. Process Res. Dev. 2018, 22, 907-917. DOI: 10.1021/acs.oprd.8b00238 | [Full Text Link]