Communication
Synthesis of Ketones by C−H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions
Dr. Silvia Roscales,
Prof. Dr. Aurelio G. Csáky,
Dr. Silvia Roscales
Instituto Pluridisciplinar, Universidad Complutense, Campus de Excelencia Internacional Moncloa, Paseo de Juan XXIII, 1, 28040 Madrid, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Aurelio G. Csáky
Instituto Pluridisciplinar, Universidad Complutense, Campus de Excelencia Internacional Moncloa, Paseo de Juan XXIII, 1, 28040 Madrid, Spain
Search for more papers by this authorDr. Silvia Roscales,
Prof. Dr. Aurelio G. Csáky,
Dr. Silvia Roscales
Instituto Pluridisciplinar, Universidad Complutense, Campus de Excelencia Internacional Moncloa, Paseo de Juan XXIII, 1, 28040 Madrid, Spain
Search for more papers by this authorCorresponding Author
Prof. Dr. Aurelio G. Csáky
Instituto Pluridisciplinar, Universidad Complutense, Campus de Excelencia Internacional Moncloa, Paseo de Juan XXIII, 1, 28040 Madrid, Spain
Search for more papers by this authorGraphical Abstract
Nitrosobenzene can simultaneously activate the C−H bonds of aldehydes and the C−B bonds of boronic acids triggering a C−C bond-forming process that leads to the synthesis of ketones via an intramolecular migration from boron to carbon. These findings constitute a transition-metal-free practical, scalable, and operationally easy method for the synthesis of ketones.
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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