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Intercepting the Banert cascade with nucleophilic fluorine: direct access to α-fluorinated NH-1,2,3-triazoles†
J. R. Alexander,P. V. Kevorkian,J. J. Topczewski
Chemical Communications Pub Date : 04/20/2021 00:00:00 , DOI:10.1039/D1CC01179K
Abstract

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%.

Graphical abstract: Intercepting the Banert cascade with nucleophilic fluorine: direct access to α-fluorinated NH-1,2,3-triazoles
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