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Synthesis of Ketones by C-H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions
Silvia Roscales1, Aurelio G Csáky1
1Instituto Pluridisciplinar, Universidad Complutense, Campus de Excelencia Internacional Moncloa, Paseo de Juan XXIII, 1, 28040, Madrid, Spain.
Abstract:
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.
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