Biomimetic reductive amination under the continuous-flow reaction conditions

Soloshonok, Vadim A.; Catt, Hector T.; Ono, Taizo

doi:10.1016/j.jfluchem.2009.10.013

Cited by 13 publications

(2 citation statements)

References 94 publications

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“…Soloshonok and co-workers 54 reported a detailed investigation into the use of a continuous flow reactor for the biomimetic reductive amination of fluorinated carbonyl compounds as a means of accessing amines and amino acids of biomedical importance. Using a column reactor packed with silicaabsorbed DBU 52, the authors were able to perform 1,3-proton shift reactions by percolating solutions of fluorinated imines (10 mol% in hexane : MeCN (4 : 1)) through the reactor at 50 1C (Scheme 22).…”

Section: Reductive Aminationsmentioning

confidence: 99%

Recent advances in micro reaction technology

2011

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Section: Reductive Aminationsmentioning

confidence: 99%

Recent advances in micro reaction technology

2011

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“…In our experience, the application of flow technology has proven to be an effective tool for the exploitation of heterogeneous catalysis in alternative reaction media, allowing achievement of high environmental efficiency . Although several protocols for the continuous-flow reductive amination of aldehydes, ketones, and nitriles have been recently reported, to the best of our knowledge, this is the first example of one-pot hydrogenation of phenol and subsequent amination carried out in batch and/or in continuous flow conditions.…”

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confidence: 98%

Domino Hydrogenation–Reductive Amination of Phenols, a Simple Process To Access Substituted Cyclohexylamines

et al. 2015

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Phenols can be efficiently reduced by sodium formate and Pd/C as the catalyst in water and in the presence of amines to give the corresponding cyclohexylamines. This reaction works at rt for 12 h or at 60 °C under microwave dielectric heating for 20 min. With the exception of aniline, primary, secondary amines, amino alcohols, and even amino acids can be used as nucleophiles. The reductive process is based on a sustainable hydrogen source and a catalyst that can be efficiently recovered and reused. The protocol was developed into a continuous-flow production of cyclohexylamines in gram scale achieving very efficient preliminary results (TON 32.7 and TOF 5.45 h(-1)).

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Application of Microreactor Methodology for Organic Synthesis

Watts

Wiles

2013

Stereoselective Synthesis of Drugs and Natural Products

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Microreactor technology is an emerging technique that enables those working in research and development to screen reactions rapidly using continuous flow, leading to the identification of reaction conditions that are suitable for use at a production level. Furthermore, in addition to using conventional reaction methodology, the inherent safety associated with the use of small reactor volumes enables users to employ reaction conditions previously thought to be too hazardous for use within a production environment.

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Biomimetic reductive amination under the continuous-flow reaction conditions

Cited by 13 publications

References 94 publications

Recent advances in micro reaction technology

Recent advances in micro reaction technology

Domino Hydrogenation–Reductive Amination of Phenols, a Simple Process To Access Substituted Cyclohexylamines

Application of Microreactor Methodology for Organic Synthesis

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