Synthesis of Ketones by C-H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions.

A method for the synthesis of ketones from aldehydes and boronic acids via a transition-metal-free C-H functionalization reaction is reported. The method employs nitrosobenzene as a reagent to drive the simultaneous activation of the boronic acid as a boronate and the activation of the C-H bond of the aldehyde as an iminium species that triggers the key C-C bond-forming step via an intramolecular migration from boron to carbon. These findings constitute a practical, scalable, and operationally straightforward method for the synthesis of ketones.