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Cooperative catalysis of cellulose nanofiber and organocatalyst in direct aldol reactions

Cellulose nanofibers (CNFs) are finding a wide range of applications in the forthcoming sustainable society because of their carbon-neutral renewability and superior physicochemical properties. Here, we first show a cooperative organocatalysis by combining TEMPO-oxidized cellulose nanofiber (TOCN) a...

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Autores principales: Kanomata, Kyohei, Tatebayashi, Naoko, Habaki, Xin, Kitaoka, Takuya
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5840413/
https://www.ncbi.nlm.nih.gov/pubmed/29511253
http://dx.doi.org/10.1038/s41598-018-22350-5
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author Kanomata, Kyohei
Tatebayashi, Naoko
Habaki, Xin
Kitaoka, Takuya
author_facet Kanomata, Kyohei
Tatebayashi, Naoko
Habaki, Xin
Kitaoka, Takuya
author_sort Kanomata, Kyohei
collection PubMed
description Cellulose nanofibers (CNFs) are finding a wide range of applications in the forthcoming sustainable society because of their carbon-neutral renewability and superior physicochemical properties. Here, we first show a cooperative organocatalysis by combining TEMPO-oxidized cellulose nanofiber (TOCN) and proline to enhance the catalytic efficiency in a direct aldol reaction. The yields of proline-catalyzed aldol products drastically increased in the presence of catalytically-inactive TOCN. This effect was also achieved by simply adding the TOCN to the reaction conditions where various proline analogues including structurally simple pyrrolidine and piperidine were used instead of proline. TOCN was superior to physically-pulverized CNF in the organocatalytic efficiency, and the nanofibrillation of cellulose microfibrils in reaction media was essential to induce the drastic enhancement in catalytic activity. The present finding will bring a new entry in the applications of CNFs, and open up a new phase in developing highly efficient molecular transformations in green chemical industries.
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spelling pubmed-58404132018-03-13 Cooperative catalysis of cellulose nanofiber and organocatalyst in direct aldol reactions Kanomata, Kyohei Tatebayashi, Naoko Habaki, Xin Kitaoka, Takuya Sci Rep Article Cellulose nanofibers (CNFs) are finding a wide range of applications in the forthcoming sustainable society because of their carbon-neutral renewability and superior physicochemical properties. Here, we first show a cooperative organocatalysis by combining TEMPO-oxidized cellulose nanofiber (TOCN) and proline to enhance the catalytic efficiency in a direct aldol reaction. The yields of proline-catalyzed aldol products drastically increased in the presence of catalytically-inactive TOCN. This effect was also achieved by simply adding the TOCN to the reaction conditions where various proline analogues including structurally simple pyrrolidine and piperidine were used instead of proline. TOCN was superior to physically-pulverized CNF in the organocatalytic efficiency, and the nanofibrillation of cellulose microfibrils in reaction media was essential to induce the drastic enhancement in catalytic activity. The present finding will bring a new entry in the applications of CNFs, and open up a new phase in developing highly efficient molecular transformations in green chemical industries. Nature Publishing Group UK 2018-03-06 /pmc/articles/PMC5840413/ /pubmed/29511253 http://dx.doi.org/10.1038/s41598-018-22350-5 Text en © The Author(s) 2018 Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/.
spellingShingle Article
Kanomata, Kyohei
Tatebayashi, Naoko
Habaki, Xin
Kitaoka, Takuya
Cooperative catalysis of cellulose nanofiber and organocatalyst in direct aldol reactions
title Cooperative catalysis of cellulose nanofiber and organocatalyst in direct aldol reactions
title_full Cooperative catalysis of cellulose nanofiber and organocatalyst in direct aldol reactions
title_fullStr Cooperative catalysis of cellulose nanofiber and organocatalyst in direct aldol reactions
title_full_unstemmed Cooperative catalysis of cellulose nanofiber and organocatalyst in direct aldol reactions
title_short Cooperative catalysis of cellulose nanofiber and organocatalyst in direct aldol reactions
title_sort cooperative catalysis of cellulose nanofiber and organocatalyst in direct aldol reactions
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5840413/
https://www.ncbi.nlm.nih.gov/pubmed/29511253
http://dx.doi.org/10.1038/s41598-018-22350-5
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