One-step Conversion of Levulinic Acid to Succinic Acid Using I(2)/t-BuOK System: The Iodoform Reaction Revisited

The iodoform reaction has long been used as a qualitative test for acetyl and/or ethanol units in organic molecules. However, its synthetic applications are quite limited. Here, we describe a tuned iodoform reaction for oxidative demethylation reaction with I(2) and t-BuOK in t-BuOH, in which in sit...

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Autores principales: Kawasumi, Ryosuke, Narita, Shodai, Miyamoto, Kazunori, Tominaga, Ken-ichi, Takita, Ryo, Uchiyama, Masanobu
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2017
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5740180/
https://www.ncbi.nlm.nih.gov/pubmed/29269768
http://dx.doi.org/10.1038/s41598-017-17116-4
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author Kawasumi, Ryosuke
Narita, Shodai
Miyamoto, Kazunori
Tominaga, Ken-ichi
Takita, Ryo
Uchiyama, Masanobu
author_facet Kawasumi, Ryosuke
Narita, Shodai
Miyamoto, Kazunori
Tominaga, Ken-ichi
Takita, Ryo
Uchiyama, Masanobu
author_sort Kawasumi, Ryosuke
collection PubMed
description The iodoform reaction has long been used as a qualitative test for acetyl and/or ethanol units in organic molecules. However, its synthetic applications are quite limited. Here, we describe a tuned iodoform reaction for oxidative demethylation reaction with I(2) and t-BuOK in t-BuOH, in which in situ-generated t-BuOI serves as the chemoselective iodinating agent. This system enables one-step conversion of levulinic acid to succinic acid, a major four-carbon chemical feedstock. This oxidative demethylation is also applicable to other compounds containing an acetyl group/ethanol unit, affording the corresponding carboxylic acids in a selective manner.
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spelling pubmed-57401802018-01-03 One-step Conversion of Levulinic Acid to Succinic Acid Using I(2)/t-BuOK System: The Iodoform Reaction Revisited Kawasumi, Ryosuke Narita, Shodai Miyamoto, Kazunori Tominaga, Ken-ichi Takita, Ryo Uchiyama, Masanobu Sci Rep Article The iodoform reaction has long been used as a qualitative test for acetyl and/or ethanol units in organic molecules. However, its synthetic applications are quite limited. Here, we describe a tuned iodoform reaction for oxidative demethylation reaction with I(2) and t-BuOK in t-BuOH, in which in situ-generated t-BuOI serves as the chemoselective iodinating agent. This system enables one-step conversion of levulinic acid to succinic acid, a major four-carbon chemical feedstock. This oxidative demethylation is also applicable to other compounds containing an acetyl group/ethanol unit, affording the corresponding carboxylic acids in a selective manner. Nature Publishing Group UK 2017-12-21 /pmc/articles/PMC5740180/ /pubmed/29269768 http://dx.doi.org/10.1038/s41598-017-17116-4 Text en © The Author(s) 2017 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
Kawasumi, Ryosuke
Narita, Shodai
Miyamoto, Kazunori
Tominaga, Ken-ichi
Takita, Ryo
Uchiyama, Masanobu
One-step Conversion of Levulinic Acid to Succinic Acid Using I(2)/t-BuOK System: The Iodoform Reaction Revisited
title One-step Conversion of Levulinic Acid to Succinic Acid Using I(2)/t-BuOK System: The Iodoform Reaction Revisited
title_full One-step Conversion of Levulinic Acid to Succinic Acid Using I(2)/t-BuOK System: The Iodoform Reaction Revisited
title_fullStr One-step Conversion of Levulinic Acid to Succinic Acid Using I(2)/t-BuOK System: The Iodoform Reaction Revisited
title_full_unstemmed One-step Conversion of Levulinic Acid to Succinic Acid Using I(2)/t-BuOK System: The Iodoform Reaction Revisited
title_short One-step Conversion of Levulinic Acid to Succinic Acid Using I(2)/t-BuOK System: The Iodoform Reaction Revisited
title_sort one-step conversion of levulinic acid to succinic acid using i(2)/t-buok system: the iodoform reaction revisited
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5740180/
https://www.ncbi.nlm.nih.gov/pubmed/29269768
http://dx.doi.org/10.1038/s41598-017-17116-4
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