Metal-Free Deoxygenation of α-Hydroxy Carbonyl Compounds

  • Author: European Journal of Organic Chemistry
  • Published Date: 19 April 2020
  • Source / Publisher: European Journal of Organic Chemistry/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: Metal-Free Deoxygenation of α-Hydroxy Carbonyl Compounds

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The conversion of C-OH bonds to C-H bonds, or deoxygenation, is an important process in organic synthesis. It can be used for the transformation of high-volume, low-value biomass into high-value chemicals and fuels. Existing protocols for deoxygenation generally use environmentally harmful metals as catalysts. The development of metal-free pathways for direct and selective deoxygenation reactions would, thus, be useful.

Anil Kumar, Panjab University, Chandigarh, India, and colleagues have developed a metal-free, direct, and selective approach for the deoxygenation of 2-hydroxy-1,2,2-triarylethanones to access 1,2,2-triarylethanones (pictured). The team used low-cost aqueous HClO4 as a Brønsted acid catalyst and triethylsilane (Et3SiH) as a soluble hydride source. The reaction was performed at 40 °C in CH2Cl2 and the desired products were obtained in good to excellent yields.

The researchers have also used the protocol to deoxygenate α-hydroxy acids and α-hydroxy esters. Mechanistically, the team  proposes the involvement of an α-carbonyl carbenium ion as an intermediate, which is then trapped by the hydride source to give the deoxygenated product.



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