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A Simple and Efficient Procedure for the Deoxygenation of Ketones via a Palladium-Catalyzed Reduction of Vinyl Mesylates

par Hansjacob, Pierre ;Audet, Florian ;Ali Ahmad, Mohamad ;Jacob, Clément ;Echeverria, Pierre-Georges;Evano, Gwilherm
Référence European Journal of Organic Chemistry
Publication Publié, 2025-12-01

Article révisé par les pairs

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Résumé :

A simple and efficient procedure for the deoxygenation of enolizable, activated ketones is reported. Upon activation as the corresponding vinyl mesylates, they are readily and easily reduced to the corresponding hydrocarbons using a particularly simple and reusable heterogeneous catalyst, palladium on carbon, under pressure of hydrogen in water, using only 10% of THF as cosolvent. A range of ketones can be readily deoxygenated using this userfriendly procedure while its synthetic potential is highlighted in a total synthesis of tanikolide in which the use of this sequence allows performing the removal of a ketone using a considerably shorter sequence compared to a previously reported procedure. As an added bonus, the intermediate vinyl mesylates are shown to be remarkably stable and easy to handle compared to the corresponding tosylates and triflates.