Fluorination of boronic acids mediated by silver(I) triflate
- PMID: 19507870
- DOI: 10.1021/ol901113t
Fluorination of boronic acids mediated by silver(I) triflate
Abstract
A regiospecific Ag-mediated fluorination reaction of aryl- and alkenylboronic acids and esters is reported. The fluorination reaction uses commercially available reagents, does not require the addition of exogenous ligands, and can be performed on a multigram scale. This report discloses the first practical reaction sequence from arylboronic acid to aryl fluorides.
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