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Parahydrogen‐Induced Polarization in Hydrogenation Reactions Mediated by a Metal‐Free Catalyst

Danila O. Zakharov, Konstantin Chernichenko, Kristina Sorochkina, Shengjun Yang, Ville‐Veikko Telkki, Timo Repo, Владимир В. Живонитко

2021Chemistry - A European Journal24 citationsDOIOpen Access PDF

Abstract

Abstract We report nuclear spin hyperpolarization of various alkenes achieved in alkyne hydrogenations with parahydrogen over a metal‐free hydroborane catalyst (HCAT). Being an intramolecular frustrated Lewis pair aminoborane, HCAT utilizes a non‐pairwise mechanism of H 2 transfer to alkynes that normally prevents parahydrogen‐induced polarization (PHIP) from being observed. Nevertheless, the specific spin dynamics in catalytic intermediates leads to the hyperpolarization of predominantly one hydrogen in alkene. PHIP enabled the detection of important HCAT‐alkyne‐H 2 intermediates through substantial 1 H, 11 B and 15 N signal enhancement and allowed advanced characterization of the catalytic process.

Topics & Concepts

Spin isomers of hydrogenHyperpolarization (physics)AlkeneAlkyneCatalysisChemistryIntramolecular forcePhotochemistryFrustrated Lewis pairInduced polarizationPolarization (electrochemistry)HydrogenLewis acids and basesStereochemistryNuclear magnetic resonance spectroscopyPhysical chemistryOrganic chemistryPhysicsElectrical resistivity and conductivityQuantum mechanicsAdvanced NMR Techniques and ApplicationsSolid-state spectroscopy and crystallographyBoron Compounds in Chemistry
Parahydrogen‐Induced Polarization in Hydrogenation Reactions Mediated by a Metal‐Free Catalyst | Litcius