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Mild Deoxygenation of Aromatic Ketones and Aldehydes over Pd/C Using Polymethylhydrosiloxane as the Reducing Agent

Volkov, Alexey (author)
Stockholms universitet,Institutionen för organisk kemi
Gustafson, Karl P. J. (author)
Stockholms universitet,Institutionen för organisk kemi
Tai, Cheuk-Wai (author)
Stockholms universitet,Institutionen för material- och miljökemi (MMK)
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Verho, Oscar (author)
Stockholms universitet,Institutionen för organisk kemi
Bäckvall, Jan-E. (author)
Stockholms universitet,Institutionen för organisk kemi
Adolfsson, Hans (author)
Stockholms universitet,Institutionen för organisk kemi
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 (creator_code:org_t)
2015-02-26
2015
English.
In: Angewandte Chemie International Edition. - : Wiley-VCH Verlagsgesellschaft. - 1433-7851 .- 1521-3773. ; 54:17, s. 5122-5126
  • Journal article (peer-reviewed)
Abstract Subject headings
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  • Herein, a practical and mild method for the deoxygenation of a wide range of benzylic aldehydes and ketones is described, which utilizes heterogeneous Pd/C as the catalyst together with the green hydride source, polymethylhydrosiloxane. The developed catalytic protocol is scalable and robust, as exemplified by the deoxygenation of ethyl vanillin, which was performed on a 30 mmol scale in an open-to-air setup using only 0.085 mol% Pd/C catalyst to furnish the corresponding deoxygenated product in 93% yield within 3 hours at room temperature. Furthermore, the Pd/C catalyst was shown to be recyclable up to 6 times without any observable decrease in efficiency and it exhibited low metal leaching under the reaction conditions.

Subject headings

NATURVETENSKAP  -- Kemi (hsv//swe)
NATURAL SCIENCES  -- Chemical Sciences (hsv//eng)

Keyword

deoxygenation
heterogeneous catalysis
ketones
palladium
silanes

Publication and Content Type

ref (subject category)
art (subject category)

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