Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 60, Issue 16, Pages 8728-8732Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202015835
Keywords
aldehydes; boron; C− C coupling; ketones; synthetic methods
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Funding
- Spanish government (MICINN) [RTI2018-096520-B-I00]
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The method reported in the study utilizes nitrosobenzene as a reagent to activate boronic acid and aldehyde C-H bond simultaneously, triggering the synthesis of ketones through intramolecular migration. This practical and scalable method provides a straightforward approach for ketone synthesis.
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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