Teaching an Old Dog New Tricks: Simple Selective and Regiodivergent Quinoline Hydrogenation

Bourriquen, Florian; Hervochon, Julien; Bartling, Stephan; Rockstroh, Nils; Fischmeister, Cédric; Junge, Kathrin; Beller, Matthias

doi:10.1021/acssuschemeng.3c04254

ACS Sustainable Chem. Eng.

2023

DOI: 10.1021/acssuschemeng.3c04254

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Teaching an Old Dog New Tricks: Simple Selective and Regiodivergent Quinoline Hydrogenation

Florian Bourriquen,

Julien Hervochon,

Stephan Bartling

et al.

Abstract: A methodology for a regiodivergent hydrogenation of quinolines is reported using broadly available and commercial supported ruthenium catalysts. cis- or trans-Decahydroquinolines are obtained in high yield and high diastereoselectivity by simple variation of the catalyst and/or reaction temperature.

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2024

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Cited by 2 publications

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Synthesis and Ring‐Closing Reactions of Aminocyclohexane Derivatives Bearing Unsaturated Side Chains at C2: Stereocontrolled Approaches to cis‐ and trans‐Fused Perhydro‐indoles and ‐quinolines

Xing,

He,

Song

et al. 2024

Eur J Org Chem

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Two epimeric pairs of N‐Ts‐protected cyclohexylamines that incorporate an unsaturated side‐chain at the C2 position have been prepared. Contrary to expectations, none of these underwent clean, photochemically‐induced intramolecular hydroamination reactions to give the corresponding perhydro‐indole or ‐quinolines. However, they did participate in efficient olefin cross metathesis (OCM) reactions with methyl crotonate. Three of the four acrylates so‐formed engaged in base‐promoted and completely diastereoselective, intramolecular aza‐Michael addition (cyclisation) reactions to give the isomeric and C2‐substituted perhydro‐indoles or ‐quinolines with the structures of these being confirmed by single‐crystal X‐ray analyses. DFT calculations generated results consistent with the observed diastereoselectivities and the proposed transition states. Manipulation of the ester groups associated with the cyclization products allowed for their conversion, inter alia, into the corresponding n‐propyl residues and thus providing novel analogues of neurotoxic alkaloids such as pumiliotoxin C.

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Synthesis and Ring‐Closing Reactions of Aminocyclohexane Derivatives Bearing Unsaturated Side Chains at C2: Stereocontrolled Approaches to cis‐ and trans‐Fused Perhydro‐indoles and ‐quinolines

Xing,

He,

Song

et al. 2024

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

Efficiency of high-loaded nickel catalysts modified by Mg in hydrogen storage/extraction using quinoline/decahydroquinoline pair as LOHC substrates

Koskin,

Zhang,

Belskaya

et al. 2024

Journal of Magnesium and Alloys

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Teaching an Old Dog New Tricks: Simple Selective and Regiodivergent Quinoline Hydrogenation

Cited by 2 publications

References 60 publications

Synthesis and Ring‐Closing Reactions of Aminocyclohexane Derivatives Bearing Unsaturated Side Chains at C2: Stereocontrolled Approaches to cis‐ and trans‐Fused Perhydro‐indoles and ‐quinolines

Synthesis and Ring‐Closing Reactions of Aminocyclohexane Derivatives Bearing Unsaturated Side Chains at C2: Stereocontrolled Approaches to cis‐ and trans‐Fused Perhydro‐indoles and ‐quinolines

Efficiency of high-loaded nickel catalysts modified by Mg in hydrogen storage/extraction using quinoline/decahydroquinoline pair as LOHC substrates

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