Library-friendly synthesis of fluorinated ketones through functionalized hydration of alkynes and investigation of the reaction mechanism

A library-friendly synthesis of α-substituted-α-fluoroketones through functionalized hydration of alkynes in one pot under mild conditions is reported. The ready availability of alkynes and organoboronic acids makes this reaction quite attractive. We also studied the key intermediate—a fluorinated cationic gold species—using in situ NMR spectroscopy and ESI-high resolution mass spectrometry.

Figure optionsDownload as PowerPoint slideHighlights
► Tandem methodology to prepare functionalized fluoroketones from alkynes.
► Gold catalyst role in functionalized hydration unveiled.
► Gold(I) undergoes a fluorine-engendered oxidation and concomitant triple bond activation.
► Mass spectrometry investigation of reaction catalysis.