Synthesis of Ketones by C−H Functionalization of Aldehydes with Boronic Acids under Transition‐Metal‐Free Conditions
Silvia Roscales, Aurelio G. Csákÿ
Abstract
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.
Topics & Concepts
ChemistryIminiumBoronic acidAldehydeIntramolecular forceSurface modificationNitrosobenzeneReagentTransition metalCombinatorial chemistryOrganic chemistryMetalationCatalysisPhysical chemistryCatalytic C–H Functionalization MethodsOrganoboron and organosilicon chemistryCatalytic Cross-Coupling Reactions