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Aqueous microdroplets containing only ketones or aldehydes undergo Dakin and Baeyer–Villiger reactions
The Dakin and Baeyer–Villiger (BV) oxidation reactions require addition of peroxides as oxidants and an acid or a base as a catalyst. Reaction times range from hours to days to obtain target products. Previously, we reported that hydrogen peroxide (H(2)O(2)) is spontaneously generated in water micro...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7439776/ https://www.ncbi.nlm.nih.gov/pubmed/32874488 http://dx.doi.org/10.1039/c9sc05112k |
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author | Gao, Dan Jin, Feng Lee, Jae Kyoo Zare, Richard N. |
author_facet | Gao, Dan Jin, Feng Lee, Jae Kyoo Zare, Richard N. |
author_sort | Gao, Dan |
collection | PubMed |
description | The Dakin and Baeyer–Villiger (BV) oxidation reactions require addition of peroxides as oxidants and an acid or a base as a catalyst. Reaction times range from hours to days to obtain target products. Previously, we reported that hydrogen peroxide (H(2)O(2)) is spontaneously generated in water microdroplets without any added chemicals or applied electrical potential. Here, we report that the Dakin and BV reactions occur in modest yields within milliseconds in aqueous microdroplets at room-temperature without the addition of external peroxides and catalysts. H(2)O(2) generation is the result of the special environment of the microdroplet surface, which promotes water autoionization. We find that increasing the content of water and decreasing the droplet size improve the product yield of the Dakin and BV reactions, supporting the contention that the amount of H(2)O(2) generated in aqueous microdroplets could induce the two reactions and the reactions occur at or near the air–water interface of the microdroplet surface. |
format | Online Article Text |
id | pubmed-7439776 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-74397762020-08-31 Aqueous microdroplets containing only ketones or aldehydes undergo Dakin and Baeyer–Villiger reactions Gao, Dan Jin, Feng Lee, Jae Kyoo Zare, Richard N. Chem Sci Chemistry The Dakin and Baeyer–Villiger (BV) oxidation reactions require addition of peroxides as oxidants and an acid or a base as a catalyst. Reaction times range from hours to days to obtain target products. Previously, we reported that hydrogen peroxide (H(2)O(2)) is spontaneously generated in water microdroplets without any added chemicals or applied electrical potential. Here, we report that the Dakin and BV reactions occur in modest yields within milliseconds in aqueous microdroplets at room-temperature without the addition of external peroxides and catalysts. H(2)O(2) generation is the result of the special environment of the microdroplet surface, which promotes water autoionization. We find that increasing the content of water and decreasing the droplet size improve the product yield of the Dakin and BV reactions, supporting the contention that the amount of H(2)O(2) generated in aqueous microdroplets could induce the two reactions and the reactions occur at or near the air–water interface of the microdroplet surface. Royal Society of Chemistry 2019-11-12 /pmc/articles/PMC7439776/ /pubmed/32874488 http://dx.doi.org/10.1039/c9sc05112k Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0) |
spellingShingle | Chemistry Gao, Dan Jin, Feng Lee, Jae Kyoo Zare, Richard N. Aqueous microdroplets containing only ketones or aldehydes undergo Dakin and Baeyer–Villiger reactions |
title | Aqueous microdroplets containing only ketones or aldehydes undergo Dakin and Baeyer–Villiger reactions
|
title_full | Aqueous microdroplets containing only ketones or aldehydes undergo Dakin and Baeyer–Villiger reactions
|
title_fullStr | Aqueous microdroplets containing only ketones or aldehydes undergo Dakin and Baeyer–Villiger reactions
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title_full_unstemmed | Aqueous microdroplets containing only ketones or aldehydes undergo Dakin and Baeyer–Villiger reactions
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title_short | Aqueous microdroplets containing only ketones or aldehydes undergo Dakin and Baeyer–Villiger reactions
|
title_sort | aqueous microdroplets containing only ketones or aldehydes undergo dakin and baeyer–villiger reactions |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7439776/ https://www.ncbi.nlm.nih.gov/pubmed/32874488 http://dx.doi.org/10.1039/c9sc05112k |
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