Advanced Synthesis and Catalysis
Advanced Synthesis and Catalysis
5 years ago

Chlorotrimethylsilane and Sodium Iodide: A Useful Combination for the Regioselective Deoxygenation of Arylalkyl-α-Diketones

Chlorotrimethylsilane and Sodium Iodide: A Useful Combination for the Regioselective Deoxygenation of Arylalkyl-α-Diketones
Mouad Alami, Ling-Zhi Yuan, Guangkuan Zhao, Abdallah Hamze, Olivier Provot
An efficient regioselective deoxygenation of arylalkyl-1,2-diketones by the couple trimethylsilylchloride/sodium iodide has been reported. In all cases, the deoxygenation takes place on the carbonyl group (Cα=O) proximal to the aromatic ring in methylene chloride at room temperature in good yields, furnishing a series of variously functionalized alkylbenzylketones. A large range of functional groups were well tolerated on the ortho-, meta- and para-positions by this mild process regardless of their electronic effects, demonstrating the general character of the present methodology. The trimethylsilylchloride/sodium iodide reducing process was also successfully applied to reduce α-ketoacid and α-ketoester substrates.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/adsc.201700276

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