Acylboronates in Polarity-Reversed Generation of Acyl Palladium(II) Intermediates

We report a catalytic cross-coupling process between aryl (pseudo)­halides and boron-based acyl anion equivalents. This mode of acylboronate reactivity represents polarity reversal, which is supported by the observation of tetracoordinated boronate and acyl palladium­(II) species by 11B, 31P NMR, and mass spectrometry. A broad scope of aliphatic and aromatic acylboronates has been examined, as well as a variety of aryl (pseudo)­halides.