AI Article Synopsis
- A new, efficient method has been developed for oxidizing terminal olefins using a Pd(ii) catalyst and MnO2, leading to β-hydroxy-methyl ketones.
- This method operates under mild conditions, ensuring good compatibility with various functional groups while maintaining high selectivity.
- Unlike previous methods that produced α,β-unsaturated ketones, this approach avoids common side reactions, demonstrating versatility in producing methyl ketones and even successfully synthesizing gingerol.
Article Abstract
Efficient and mild reaction conditions for Wacker-type oxidation of terminal olefins of less explored homoallyl alcohols to β-hydroxy-methyl ketones have been developed by using a Pd(ii) catalyst and MnO2 as a co-oxidant. The method involves mild reaction conditions and shows good functional group compatibility along with high regio- and chemoselectivity. While our earlier system of PdCl2/CrO3/HCl produced α,β-unsaturated ketones from homoallyl alcohols, the present method provided orthogonally the β-hydroxy-methyl ketones. No overoxidation or elimination of benzylic and/or β-hydroxy groups was observed. The method could be extended to the oxidation of simple terminal olefins as well, to methyl ketones, displaying its versatility. An application to the regioselective synthesis of gingerol is demonstrated.
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| http://dx.doi.org/10.1039/d0ob01344g | DOI Listing |
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