NFSI-participated intermolecular aminoazidation of alkene through iron catalysis.

Published on May 2, 2018in Organic and Biomolecular Chemistry3.412
· DOI :10.1039/C8OB00699G
Bowen Lei6
Estimated H-index: 6
(Sichuan University),
Xiaojiao Wang5
Estimated H-index: 5
(Sichuan University)
+ 2 AuthorsZiyuan Li11
Estimated H-index: 11
(Sichuan University)
An iron-catalysed intermolecular vicinal aminoazidation of alkenes, using N-fluorobenzenesulfonimide (NFSI) and trimethylsilyl azide (TMSN3) as the imidating and azidating reagents respectively, is described, which could potentially provide a valuable route toward diverse vicinal diamine derivatives of great significance in medicinal chemistry and organic synthesis. Such iron-catalysed aminative bisfunctionalization of alkene with NFSI has not yet been reported before. Comparing to previously employed copper or palladium catalysts, the iron catalyst, FeCl2, was demonstrated to be a good alternative for its comparable efficiency and broad alkene scope. Preliminary mechanistic study suggested that this iron-catalysed reaction is realized through radical process.
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