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Reversible Hyperpolarization of Ketoisocaproate Using Sulfoxide‐containing Polarization Transfer Catalysts

Ben. J. Tickner, Fadi Ahwal, Adrian C. Whitwood, Simon B. Duckett

2020ChemPhysChem18 citationsDOIOpen Access PDF

Abstract

Abstract The substrate scope of sulfoxide‐containing magnetisation transfer catalysts is extended to hyperpolarize α ‐ketoisocaproate and α ‐ketoisocaproate‐1‐[ 13 C]. This is achieved by forming [Ir(H) 2 ( κ 2 ‐ketoisocaproate)( N ‐heterocyclic carbene)(sulfoxide)] which transfers latent magnetism from p ‐H 2 via the signal amplification by reversible exchange (SABRE) process. The effect of polarization transfer field on the formation of enhanced 13 C magnetization is evaluated. Consequently, performing SABRE in a 0.5 μT field enabled most efficient magnetisation transfer. 13 C NMR signals for α ‐ketoisocaproate‐1‐[ 13 C] in methanol‐ d 4 are up to 985‐fold more intense than their traditional Boltzmann derived signal intensity (0.8 % 13 C polarisation). Single crystal X‐ray diffraction reveals the formation of the novel catalyst decomposition products [Ir( μ ‐H)(H) 2 (IMes)(SO(Ph)(Me) 2 )] 2 and [(Ir(H) 2 (IMes)(SO(Me) 2 )) 2 ( μ ‐S)] when the sulfoxides methylphenylsulfoxide and dimethylsulfoxide are used respectively.

Topics & Concepts

Hyperpolarization (physics)ChemistryCatalysisPolarization (electrochemistry)PhotochemistryBiophysicsNuclear magnetic resonance spectroscopyStereochemistryOrganic chemistryPhysical chemistryBiologyAdvanced NMR Techniques and ApplicationsSolid-state spectroscopy and crystallographySynthesis and Properties of Aromatic Compounds