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Probing the hydrogenation of vinyl sulfoxides using para-hydrogen

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  • Benjamin James Tickner
  • Simon Duckett
  • Rachel Roberta Parker
  • Adrian C. Whitwood


Publication details

DateAccepted/In press - 6 Oct 2019
DateE-pub ahead of print (current) - 14 Nov 2019
Issue number22
Early online date14/11/19
Original languageEnglish


Vinyl sulfoxides are an important functional group used in a wide range of organic transformations. Here, we use [IrCl(COD)(IMes)] where IMes = 1,3-bis(2,4,6-trimethyl-phenyl)imidazole-2-ylidene and COD = cis,cis-1,5-cyclooctadiene to rapidly hydrogenate phenylvinylsulfoxide. We use ParaHydrogen Induced Hyperpolarization (PHIP) to follow this reaction with [IrCl(H)2(IMes)(S(O)(Ph)(Et))2] dominating in the later stages. Decomposition to form the reduced C-S bond cleaved product [Ir2(H)3(κ2-H)(κ2-SPh)2(IMes)2(S(Et)(Ph)O)] limits turnover. The related product [Ir2(H)4(κ2-S)(IMes)2(S(O)(CH2Ph)2)2] is formed from dibenzylsulfoxide demonstrating the wider utility of this transformation.

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© 2019 American Chemical Society

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