Tethering chiral Rh diene complexes inside mesoporous solids: experimental and theoretical study of substituent, pore and linker effects on asymmetric catalysis

Kirchhof, Manuel; Gugeler, Katrin; Beurer, Ann-Katrin; Fischer, Felix Richard; Batman, Derman; Bauch, Soeren M.; Kolin, Sofia; Nicholas, Elliot; Schoch, Roland; Vogler, Charlotte; Kousik, Shravan R.; Zens, Anna; Plietker, Bernd; Atanasova, Petia; Naumann, Stefan; Bauer, Matthias; Bruckner, Johanna R.; Traa, Yvonne; Kästner, Johannes; Laschat, Sabine

doi:10.1039/d3cy00381g

Catal. Sci. Technol.

2023

DOI: 10.1039/d3cy00381g

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Tethering chiral Rh diene complexes inside mesoporous solids: experimental and theoretical study of substituent, pore and linker effects on asymmetric catalysis

Manuel Kirchhof,

Katrin Gugeler,

Ann-Katrin Beurer

et al.

Abstract: Understanding confinement effects in molecular heterogeneous catalysis is a challenging task. In a combined experimental and theoretical approach, we studied the influence of the type, polarity, pore size and shape...

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2024

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Asymmetric Rh Diene Catalysis under Confinement: Isoxazole Ring‐Contraction in Mesoporous Solids

Marshall,

Dilruba,

Beurer

et al. 2024

Eur J Org Chem

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Covalent immobilization of chiral dienes in mesoporous solids for asymmetric heterogeneous catalysis is highly attractive. In order to study confinement effects in bimolecular vs monomolecular reactions, a series of pseudo‐C2‐symmetrical tetrahydropentalenes was synthesized and immobilized via click reaction on different mesoporous solids (silica, carbon, covalent organic frameworks) and compared with homogeneous conditions. Two types of Rh‐catalyzed reactions were studied: (a) bimolecular nucleophilic 1,2‐additions of phenylboroxine to N‐tosylimine and (b) monomolecular isomerization of isoxazole to 2H‐azirne. Polar support materials performed better than non‐polar ones. Under confinement, bimolecular reactions showed decreased yields, whereas yields in monomolecular reactions were only little affected. Regarding enantioselectivity the opposite trend was observed, i.e. effective enantiocontrol for bimolecular reactions but only little control for monomolecular reactions was found.

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Asymmetric Rh Diene Catalysis under Confinement: Isoxazole Ring‐Contraction in Mesoporous Solids

Marshall,

Dilruba,

Beurer

et al. 2024

Eur J Org Chem

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show abstract

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Tethering chiral Rh diene complexes inside mesoporous solids: experimental and theoretical study of substituent, pore and linker effects on asymmetric catalysis

Abstract: Understanding confinement effects in molecular heterogeneous catalysis is a challenging task. In a combined experimental and theoretical approach, we studied the influence of the type, polarity, pore size and shape...

Cited by 1 publication

References 77 publications

Asymmetric Rh Diene Catalysis under Confinement: Isoxazole Ring‐Contraction in Mesoporous Solids

Asymmetric Rh Diene Catalysis under Confinement: Isoxazole Ring‐Contraction in Mesoporous Solids

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