Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor

We have successfully synthesized piperidine and pyrrolidine derivatives by electroreductive cyclization using readily available imine and terminal dihaloalkanes in a flow microreactor. Reduction of the substrate imine on the cathode proceeded efficiently due to the large specific surface area of the...

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Detalles Bibliográficos
Autores principales: Naito, Yuki, Shida, Naoki, Atobe, Mahito
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8978912/
https://www.ncbi.nlm.nih.gov/pubmed/35422883
http://dx.doi.org/10.3762/bjoc.18.39
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author Naito, Yuki
Shida, Naoki
Atobe, Mahito
author_facet Naito, Yuki
Shida, Naoki
Atobe, Mahito
author_sort Naito, Yuki
collection PubMed
description We have successfully synthesized piperidine and pyrrolidine derivatives by electroreductive cyclization using readily available imine and terminal dihaloalkanes in a flow microreactor. Reduction of the substrate imine on the cathode proceeded efficiently due to the large specific surface area of the microreactor. This method provided target compounds in good yields compared to a conventional batch-type reaction. Furthermore, piperidine and pyrrolidine derivatives could be obtained on preparative scale by continuous electrolysis for approximately 1 hour.
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spelling pubmed-89789122022-04-13 Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor Naito, Yuki Shida, Naoki Atobe, Mahito Beilstein J Org Chem Full Research Paper We have successfully synthesized piperidine and pyrrolidine derivatives by electroreductive cyclization using readily available imine and terminal dihaloalkanes in a flow microreactor. Reduction of the substrate imine on the cathode proceeded efficiently due to the large specific surface area of the microreactor. This method provided target compounds in good yields compared to a conventional batch-type reaction. Furthermore, piperidine and pyrrolidine derivatives could be obtained on preparative scale by continuous electrolysis for approximately 1 hour. Beilstein-Institut 2022-03-29 /pmc/articles/PMC8978912/ /pubmed/35422883 http://dx.doi.org/10.3762/bjoc.18.39 Text en Copyright © 2022, Naito et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Naito, Yuki
Shida, Naoki
Atobe, Mahito
Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor
title Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor
title_full Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor
title_fullStr Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor
title_full_unstemmed Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor
title_short Synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor
title_sort synthesis of piperidine and pyrrolidine derivatives by electroreductive cyclization of imine with terminal dihaloalkanes in a flow microreactor
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8978912/
https://www.ncbi.nlm.nih.gov/pubmed/35422883
http://dx.doi.org/10.3762/bjoc.18.39
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AT shidanaoki synthesisofpiperidineandpyrrolidinederivativesbyelectroreductivecyclizationofiminewithterminaldihaloalkanesinaflowmicroreactor
AT atobemahito synthesisofpiperidineandpyrrolidinederivativesbyelectroreductivecyclizationofiminewithterminaldihaloalkanesinaflowmicroreactor

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