1,4-Fluoroamination of 1,3-Enynes en Route to Fluorinated Allenes

The regioselective synthesis of fluorinated allenes via a metal-free 1,4-fluoroamination of 1,3-enynes is presented. This method employs commercially available N-fluorobenzenesulfonimide serving as both the nitrogen source and the fluorine source, affording access to various tetrasubstituted allenes...

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Bibliographic Details
Published in:Organic letters 2020-07, Vol.22 (13), p.5261-5265
Main Authors: Zhang, Qi, Muhammad, Munira Taj, Chiou, Mong-Feng, Jiao, Yihang, Bao, Hongli, Li, Yajun
Format: Article
Language:English
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Summary:The regioselective synthesis of fluorinated allenes via a metal-free 1,4-fluoroamination of 1,3-enynes is presented. This method employs commercially available N-fluorobenzenesulfonimide serving as both the nitrogen source and the fluorine source, affording access to various tetrasubstituted allenes in a straightforward and atom-economic pathway. Preliminary mechanistic studies and theoretical studies revealed that this reaction might undergo an intimate ion-pair mechanism.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01953