Efficient metal-free conversion of glucose to 5-hydroxymethylfurfural using a boronic acid
Abstract 5-Hydroxymethylfurfural (HMF), which can be synthesized from hexose sugars without rearrangement of their carbon framework, is a key platform chemical that is readily convertible into fuels and chemicals that are now derived from petroleum. Methods to convert glucose, which i...
| Main Authors: | , |
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| Other Authors: | |
| Format: | Article |
| Language: | English |
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Springer Berlin Heidelberg
2021
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| Online Access: | https://hdl.handle.net/1721.1/131569 |
| _version_ | 1811069015860183040 |
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| author | Graham, Brian J Raines, Ronald T |
| author2 | Massachusetts Institute of Technology. Department of Chemistry |
| author_facet | Massachusetts Institute of Technology. Department of Chemistry Graham, Brian J Raines, Ronald T |
| author_sort | Graham, Brian J |
| collection | MIT |
| description | Abstract
5-Hydroxymethylfurfural (HMF), which can be synthesized from hexose sugars without rearrangement of their carbon framework, is a key platform chemical that is readily convertible into fuels and chemicals that are now derived from petroleum. Methods to convert glucose, which is readily accessible from cellulose, to HMF typically rely on toxic heavy metals or harsh acidic conditions and often give low yields or low selectivity. Here, we report on a mild, efficient, and metal-free process that uses an organocatalyst, 2-carboxyphenylboronic acid, along with small amounts of chloride ion to effect the selective transformation of glucose to HMF. |
| first_indexed | 2024-09-23T08:04:21Z |
| format | Article |
| id | mit-1721.1/131569 |
| institution | Massachusetts Institute of Technology |
| language | English |
| last_indexed | 2024-09-23T08:04:21Z |
| publishDate | 2021 |
| publisher | Springer Berlin Heidelberg |
| record_format | dspace |
| spelling | mit-1721.1/1315692023-02-17T15:19:07Z Efficient metal-free conversion of glucose to 5-hydroxymethylfurfural using a boronic acid Graham, Brian J Raines, Ronald T Massachusetts Institute of Technology. Department of Chemistry Abstract 5-Hydroxymethylfurfural (HMF), which can be synthesized from hexose sugars without rearrangement of their carbon framework, is a key platform chemical that is readily convertible into fuels and chemicals that are now derived from petroleum. Methods to convert glucose, which is readily accessible from cellulose, to HMF typically rely on toxic heavy metals or harsh acidic conditions and often give low yields or low selectivity. Here, we report on a mild, efficient, and metal-free process that uses an organocatalyst, 2-carboxyphenylboronic acid, along with small amounts of chloride ion to effect the selective transformation of glucose to HMF. 2021-09-20T17:20:25Z 2021-09-20T17:20:25Z 2018-12-04 2020-09-24T21:08:58Z Article http://purl.org/eprint/type/JournalArticle https://hdl.handle.net/1721.1/131569 en https://doi.org/10.1007/s13399-018-0346-2 Creative Commons Attribution-Noncommercial-Share Alike http://creativecommons.org/licenses/by-nc-sa/4.0/ Springer-Verlag GmbH Germany, part of Springer Nature application/pdf Springer Berlin Heidelberg Springer Berlin Heidelberg |
| spellingShingle | Graham, Brian J Raines, Ronald T Efficient metal-free conversion of glucose to 5-hydroxymethylfurfural using a boronic acid |
| title | Efficient metal-free conversion of glucose to 5-hydroxymethylfurfural using a boronic acid |
| title_full | Efficient metal-free conversion of glucose to 5-hydroxymethylfurfural using a boronic acid |
| title_fullStr | Efficient metal-free conversion of glucose to 5-hydroxymethylfurfural using a boronic acid |
| title_full_unstemmed | Efficient metal-free conversion of glucose to 5-hydroxymethylfurfural using a boronic acid |
| title_short | Efficient metal-free conversion of glucose to 5-hydroxymethylfurfural using a boronic acid |
| title_sort | efficient metal free conversion of glucose to 5 hydroxymethylfurfural using a boronic acid |
| url | https://hdl.handle.net/1721.1/131569 |
| work_keys_str_mv | AT grahambrianj efficientmetalfreeconversionofglucoseto5hydroxymethylfurfuralusingaboronicacid AT rainesronaldt efficientmetalfreeconversionofglucoseto5hydroxymethylfurfuralusingaboronicacid |