Flow Giese reaction using cyanoborohydride as a radical mediator

Tin-free Giese reactions, employing primary, secondary, and tertiary alkyl iodides as radical precursors, ethyl acrylate as a radical trap, and sodium cyanoborohydride as a radical mediator, were examined in a continuous flow system. With the use of an automated flow microreactor, flow reaction cond...

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Detalles Bibliográficos
Autores principales: Fukuyama, Takahide, Kawamoto, Takuji, Kobayashi, Mikako, Ryu, Ilhyong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778382/
https://www.ncbi.nlm.nih.gov/pubmed/24062844
http://dx.doi.org/10.3762/bjoc.9.208
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author Fukuyama, Takahide
Kawamoto, Takuji
Kobayashi, Mikako
Ryu, Ilhyong
author_facet Fukuyama, Takahide
Kawamoto, Takuji
Kobayashi, Mikako
Ryu, Ilhyong
author_sort Fukuyama, Takahide
collection PubMed
description Tin-free Giese reactions, employing primary, secondary, and tertiary alkyl iodides as radical precursors, ethyl acrylate as a radical trap, and sodium cyanoborohydride as a radical mediator, were examined in a continuous flow system. With the use of an automated flow microreactor, flow reaction conditions for the Giese reaction were quickly optimized, and it was found that a reaction temperature of 70 °C in combination with a residence time of 10–15 minutes gave good yields of the desired addition products.
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spelling pubmed-37783822013-09-23 Flow Giese reaction using cyanoborohydride as a radical mediator Fukuyama, Takahide Kawamoto, Takuji Kobayashi, Mikako Ryu, Ilhyong Beilstein J Org Chem Letter Tin-free Giese reactions, employing primary, secondary, and tertiary alkyl iodides as radical precursors, ethyl acrylate as a radical trap, and sodium cyanoborohydride as a radical mediator, were examined in a continuous flow system. With the use of an automated flow microreactor, flow reaction conditions for the Giese reaction were quickly optimized, and it was found that a reaction temperature of 70 °C in combination with a residence time of 10–15 minutes gave good yields of the desired addition products. Beilstein-Institut 2013-09-03 /pmc/articles/PMC3778382/ /pubmed/24062844 http://dx.doi.org/10.3762/bjoc.9.208 Text en Copyright © 2013, Fukuyama et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Letter
Fukuyama, Takahide
Kawamoto, Takuji
Kobayashi, Mikako
Ryu, Ilhyong
Flow Giese reaction using cyanoborohydride as a radical mediator
title Flow Giese reaction using cyanoborohydride as a radical mediator
title_full Flow Giese reaction using cyanoborohydride as a radical mediator
title_fullStr Flow Giese reaction using cyanoborohydride as a radical mediator
title_full_unstemmed Flow Giese reaction using cyanoborohydride as a radical mediator
title_short Flow Giese reaction using cyanoborohydride as a radical mediator
title_sort flow giese reaction using cyanoborohydride as a radical mediator
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778382/
https://www.ncbi.nlm.nih.gov/pubmed/24062844
http://dx.doi.org/10.3762/bjoc.9.208
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AT ryuilhyong flowgiesereactionusingcyanoborohydrideasaradicalmediator

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