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

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%.

SUBMITTER: Alexander JR

PROVIDER: S-EPMC8201930 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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

Alexander J R JR Kevorkian P V PV Topczewski J J JJ

Chemical communications (Cambridge, England) 20210501 41

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%. ...[more]

PMID: 33890592

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