Enantioselective Reduction of 1-Naphthamides by Electrochemical Reduction and Catalytic Asymmetric Hydrogenation in Tandem

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: March 13, 2025

Chiral 1-tetrahydronaphthamides are the core structures of many bioactive molecules, yet their efficient asymmetric synthesis from a simple feedstock remains challenge. Herein, we present one-pot strategy that combines electrochemical reduction and ruthenium-catalyzed hydrogenation to achieve enantioselective 1-naphthalenamides chiral 1-tetrahydronaphthamides. The protocol provides practical platform for selectively constructing high-value tetrahydronaphthenes readily available naphthalene feedstock, thereby expanding scope hydrogenation. synthetic utility this is further demonstrated through molecules.

Language: Английский

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A meta-learning approach for selectivity prediction in asymmetric catalysis

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: April 15, 2025

Abstract Transition metal-catalyzed asymmetric reactions are of high contemporary importance in organic synthesis. Recently, machine learning (ML) has shown promise accelerating the development newer catalytic protocols. However, need for large amount experimental data can present a bottleneck implementing ML models. Here, we propose meta-learning workflow that harness literature-derived to extract shared reaction features and requires only few examples predict outcome new reactions. Prototypical networks used as method enantioselectivity hydrogenation olefins. This model consistently provides significant performance improvement over other popular methods such random forests graph neural networks. The our meta-model is analyzed with varying sizes training demonstrate its utility even limited data. A good on an out-of-sample test set further indicates general applicability approach. We believe this work will provide leap forward identifying promising early phases when minimal available.

Language: Английский

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A recyclable rhodium catalyst anchored onto a bipyridine covalent triazine framework for transfer hydrogenation of N-heteroarenes in water

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(8), P. 3267 - 3277

Published: Jan. 1, 2023

Bipyridine covalent triazine framework (bpyCTF) was used as a support material for the development of highly efficient Rh catalyst. The heterogeneous catalyst applied both batch and flow transfer hydrogenation various N-heteroarenes.

Language: Английский

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Scalable and Selective Electrochemical Hydrogenation of Polycyclic Arenes

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(32)

Published: June 21, 2024

Abstract The reduction of aromatic compounds constitutes a fundamental and ongoing area investigation. selective polycyclic to give either fully or partially reduced products remains challenge, especially in applications complex molecules at scale. Herein, we present electrochemical hydrogenation arenes conducted under mild conditions. A noteworthy achievement this approach is the ability finely control both complete partial specific rings within by judiciously varying reaction solvents. Mechanistic investigations elucidate pivotal role played situ proton generation interface regulation governing selectivity. reductive conditions show very high level functional‐group tolerance. Furthermore, methodology represents an easily scalable (demonstrated 1 kg scale starting material) using flow chemistry key intermediates for synthesis drugs.

Language: Английский

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Transition Metal Catalyzed Carbocycle-Selective Asymmetric Hydrogenation of Aromatic Rings

Chinese Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 44(7), P. 2063 - 2063

Published: Jan. 1, 2024

Language: Английский

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