American Chemical Society
om9b00610_si_001.pdf (1.53 MB)

Probing the Hydrogenation of Vinyl Sulfoxides Using para-Hydrogen

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journal contribution
posted on 2019-11-14, 20:47 authored by Ben J. Tickner, Rachel R. Parker, Adrian C. Whitwood, Simon B. Duckett
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 para-hydrogen-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 cleavage product [Ir2(H)32-H)­(κ2-SPh)2(IMes)2(S­(Et)­(Ph)­O)] limits turnover. The related product [Ir2(H)42-S)­(IMes)2(S­(O)­(CH2Ph)2)2] is formed from dibenzylsulfoxide, demonstrating the wider utility of this transformation.