Probing the hydrogenation of vinyl sulfoxides using para-hydrogen

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Full text download(s)

acs.organomet.9b00610
1.53 MB, PDF document

Published copy (DOI)

10.1021/acs.organomet.9b00610

Author(s)

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

Department/unit(s)

Chemistry

Publication details

Journal	Organometallics
Date	Accepted/In press - 6 Oct 2019
Date	E-pub ahead of print (current) - 14 Nov 2019
Issue number	22
Volume	38
Early online date	14/11/19
Original language	English

Abstract

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.