Catalytic hydrogenative dechlorination reaction for efficient synthesis of a key intermediate of SDHI fungicides under continuous-flow conditions

Ishitani, Haruro; Kawase, Tomoya; Das, Amrita; Kobayashi, Shū

doi:10.1039/d3cy00182b

Cited by 3 publications

(3 citation statements)

References 29 publications

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“…Scanning tunneling electron microscopy (STEM) images revealed smaller palladium nanoparticles in the 0.05 mmol/g DMPSi–Pd/AC catalyst compared to those in the 0.1 mmol/g version (Figures S5–S8). On the basis of previous studies indicating that calcium phosphate creates more electron-rich palladium species suitable for hydrogenolysis via oxidative addition, we proposed that it might be beneficial for that pathway. In contrast, for reductive amination involving hydrogenation of imine/iminium intermediates, calcium phosphate appeared to have a minimal impact on catalytic activity.…”

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confidence: 97%

“…Interestingly, DMPSi−Pd/AC exhibited superior activity (green line) compared to that of the AC−CP-supported catalyst, contradicting our earlier observations. 41,43 Furthermore, the Pd loading significantly impacted catalytic activity. DMPSi−Pd/AC with a Pd loading of 0.05 mmol/g afforded a >70% yield of 3a after yield stabilization (purple line).…”

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confidence: 99%

“…Inspired by the unique properties of the flow reaction environment, our group has been developing active and robust heterogeneous catalysts. Among them, polysilane-modified metal nanoparticle catalysts have demonstrated high activity in various hydrogenation reactions. − In most cases, these catalysts outperformed commercially available ones, enabling efficient transformations under mild flow conditions. These achievements motivated us to develop suitable catalysts for reductive N-alkylation with ketones under continuous-flow conditions.…”

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confidence: 99%

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Reductive N-Alkylation of Amines with Ketones Using Heterogeneous Polysilane–Palladium Catalysts under Continuous-Flow Conditions

Senzaki,

Saito,

Kobayashi

2024

Org. Lett.

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This work reports a continuous-flow reductive N-alkylation of amines with ketones using molecular hydrogen. The reaction, performed with highly active polysilane-modified heterogeneous palladium catalysts, enables the efficient synthesis of diversely substituted amines under mild flow conditions. The developed catalyst exhibits sustained activity for 5 days (turnover number of >2400). Moreover, the utility of the method is demonstrated by the synthesis of a key intermediate of the active pharmaceutical ingredient teneligliptin.

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confidence: 97%

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confidence: 99%

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confidence: 99%

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Reductive N-Alkylation of Amines with Ketones Using Heterogeneous Polysilane–Palladium Catalysts under Continuous-Flow Conditions

Senzaki,

Saito,

Kobayashi

2024

Org. Lett.

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Continuous Flow Synthesis of 4‐methyl‐3‐oxo‐n‐phenyl‐pentanamide

He,

Li,

Peng

et al. 2024

ChemistrySelect

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Abstract4‐methyl‐3‐oxo‐n‐phenyl‐pentanamide, as a crucial component of atorvastatin calcium, often generates a large amount of by‐products in conventional synthesis. Here, we first developed a continuous microflow system for the continuous flow synthesis of 4‐methyl‐3‐oxo‐n‐phenyl‐pentanamide. Compared to traditional batch reactors, the reaction time was reduced by 1/12 in the microreactor. Using this device, the kinetic parameters of the reaction were determined, and a reaction kinetics model was established to investigate the effects of channel geometry and material inlet velocity on the entire reaction system. Furthermore, we studied the subsequent reactions and successfully established a fully continuous synthesis device, where the two‐step continuous flow chemical reactions were achieved at 40 minutes and a total yield of 32 %.

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Reduction of Non-CO2 Greenhouse Gas Emissions by Catalytic Processes

Centi,

Perathoner

2024

Handbook of Climate Change Mitigation and Adaptation

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Catalytic hydrogenative dechlorination reaction for efficient synthesis of a key intermediate of SDHI fungicides under continuous-flow conditions

Abstract: Selective hydrodechlorination reactions under continuous-flow conditions for the synthesis of SDHI fungicide sintemediate was investigated using originally developed heterogeneous Pd catalysts. Under optimal reaction conditions accompanying use of tetrabutylammonium acetate,...

Cited by 3 publications

References 29 publications

Reductive N-Alkylation of Amines with Ketones Using Heterogeneous Polysilane–Palladium Catalysts under Continuous-Flow Conditions

Reductive N-Alkylation of Amines with Ketones Using Heterogeneous Polysilane–Palladium Catalysts under Continuous-Flow Conditions

Continuous Flow Synthesis of 4‐methyl‐3‐oxo‐n‐phenyl‐pentanamide

Reduction of Non-CO2 Greenhouse Gas Emissions by Catalytic Processes

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