Asymmetric Heterogeneous Catalysis

doi:10.1002/9781118880173.ch7

Chirality at Solid Surfaces 2018

DOI: 10.1002/9781118880173.ch7

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Asymmetric Heterogeneous Catalysis

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2022

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Adsorption and Reactivity of Chiral Modifiers in Heterogeneous Catalysis: 1-(1-Naphthyl)ethylamine on Pt Surfaces

Wang

Fernández-Escamilla²,

Guerrero-Sánchez³

et al. 2022

ACS Catal.

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The adsorption from solution onto a Pt surface of 1-(1naphthyl)ethylamine (1-NEA), a chiral modifier used to introduce enantioselectivity in catalytic hydrogenation reactions, as well as its subsequent chemical reactivity, was characterized by a combination of kinetic catalytic measurements, surface-science experiments, and quantum mechanics calculations. By using both 1 H NMR and gas chromatography/mass spectrometry detection, it was determined that 1-NEA can undergo H-D exchange with D 2 in solution when promoted by supported heterogeneous Pt catalysts. In situ infrared absorption spectroscopy studies at the solid−liquid interface afforded the detection of vibrational features indicative of the formation of N−D bonds, and quantum mechanics calculations helped with the peak assignment and provided evidence supporting an H-D exchange mechanism involving the formation of an intermediate-adsorbed protonated 1-NEA species. The reaction proved to be general, as it was observed with r-and s-1-NEA, r-and s-2-NEA, and cinchonine, and on Pt/SiO 2 and Pt/ Al 2 O 3 catalysts. NEA adsorption and protonation through the amine N atom explain a number of reported but previously not fully understood observations and provide a way to envision the mechanism by which the NEA molecule bestows enantioselectivity to Pt hydrogenation catalysts.

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Adsorption and Reactivity of Chiral Modifiers in Heterogeneous Catalysis: 1-(1-Naphthyl)ethylamine on Pt Surfaces

Wang

Fernández-Escamilla²,

Guerrero-Sánchez³

et al. 2022

ACS Catal.

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show abstract

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Asymmetric Heterogeneous Catalysis

Cited by 1 publication

References 61 publications

Adsorption and Reactivity of Chiral Modifiers in Heterogeneous Catalysis: 1-(1-Naphthyl)ethylamine on Pt Surfaces

Adsorption and Reactivity of Chiral Modifiers in Heterogeneous Catalysis: 1-(1-Naphthyl)ethylamine on Pt Surfaces

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