Intercepting the Banert cascade with nucleophilic fluorine: direct access to α-fluorinated N H-1,2,3-triazoles

The treatment of propargylic azides with silver(i) fluoride in acetonitrile was found to yield α-fluorinated NH-1,2,3-triazoles via the Banert cascade. The reaction was regioselective and the products result from an initial [3,3] rearrangement. The reaction is demonstrated on >15 examples with yi...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2021-05, Vol.57 (41), p.5024-5027
Main Authors: Alexander, J R, Kevorkian, P V, Topczewski, J J
Format: Article
Language:English
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Summary:The treatment of propargylic azides with silver(i) fluoride in acetonitrile was found to yield α-fluorinated NH-1,2,3-triazoles via the Banert cascade. The reaction was regioselective and the products result from an initial [3,3] rearrangement. The reaction is demonstrated on >15 examples with yields ranging from 37% to 86%.
ISSN:1359-7345
1364-548X
DOI:10.1039/d1cc01179k