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Synthesis

Grab-And-Go Palladium Catalyst

Novel nanoparticle catalyst pulls thiols and selenols from mixtures and couples them with alkynes to make vinyl compounds

by Stephen K. Ritter
April 16, 2012 | A version of this story appeared in Volume 90, Issue 16

Chemists have developed a palladium-based nanoparticle catalyst with the unprecedented ability to pluck thiols and selenols from a chemical mixture and then use them in an organic synthesis (J. Am. Chem. Soc., DOI: 10.1021/ja210596w). The method could lead to a more efficient process for selectively removing sulfur compounds from petroleum during oil refining, which is undertaken to avoid catalyst fouling and reduce pollution from burning gasoline and other fuels. The current hydrodesulfurization process converts sulfur compounds to hydrogen sulfide and then elemental sulfur. The sulfur can be used as a chemical reagent, but it typically piles up outside refineries as waste. Seeking a more sustainable option, a team led by Valentin P. Ananikov of the Russian Academy of Sciences and Djamaladdin G. Musaev of Emory University discovered that mixing Pd[OC(O)CH3]2 with thiols and selenols (RSH/RSeH) and acetylenic hydrocarbons generates a new type of catalyst. The catalyst self-assembles into nanoparticles made up of a network of palladium atoms interspersed with thiol and selenol molecules. It subsequently facilitates selective addition of thiols and selenols to the acetylenic compounds to form the targeted vinyl products (shown), which could be used to make polymers and various other organic compounds.

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