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Selective Oxidative Cleavage of the C–C Bond in α,β-Epoxy Ketone into Carbonyl Compounds
[Image: see text] This method afforded aromatic carbonyl compounds under TBHP via selective oxidative cleavage of the C–C bond in α,β-epoxy ketones. Aromatic acid came from the aroyl section, and aromatic aldehyde came from the other aromatic group. TBHP acted as a free radical initiator and oxidant...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2022
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9245109/ https://www.ncbi.nlm.nih.gov/pubmed/35785280 http://dx.doi.org/10.1021/acsomega.2c01464 |
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author | Jiang, Bing Li, Huai-Zhu Li, Rui-Jun Zhang, Jianye Zhang, Yun-Xiao |
author_facet | Jiang, Bing Li, Huai-Zhu Li, Rui-Jun Zhang, Jianye Zhang, Yun-Xiao |
author_sort | Jiang, Bing |
collection | PubMed |
description | [Image: see text] This method afforded aromatic carbonyl compounds under TBHP via selective oxidative cleavage of the C–C bond in α,β-epoxy ketones. Aromatic acid came from the aroyl section, and aromatic aldehyde came from the other aromatic group. TBHP acted as a free radical initiator and oxidant. The reaction within the solvent went through a ring-opening addition, cleavage of the C–C bond in the ethylene oxide section, and oxidation, affording the target compounds in moderate to good yields. The HPLC yield of aromatic aldehyde was up to 91%. The HPLC yield of aromatic acid was up to 99%. The reaction under solvent-free conditions gave two kinds of aromatic acids coming from different moieties of α,β-epoxy ketone via the further oxidation of aromatic aldehyde. The substituent effect was discussed, and the reaction mechanism was proposed. This method allowed the reaction to occur in a simple system metal-free. |
format | Online Article Text |
id | pubmed-9245109 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-92451092022-07-01 Selective Oxidative Cleavage of the C–C Bond in α,β-Epoxy Ketone into Carbonyl Compounds Jiang, Bing Li, Huai-Zhu Li, Rui-Jun Zhang, Jianye Zhang, Yun-Xiao ACS Omega [Image: see text] This method afforded aromatic carbonyl compounds under TBHP via selective oxidative cleavage of the C–C bond in α,β-epoxy ketones. Aromatic acid came from the aroyl section, and aromatic aldehyde came from the other aromatic group. TBHP acted as a free radical initiator and oxidant. The reaction within the solvent went through a ring-opening addition, cleavage of the C–C bond in the ethylene oxide section, and oxidation, affording the target compounds in moderate to good yields. The HPLC yield of aromatic aldehyde was up to 91%. The HPLC yield of aromatic acid was up to 99%. The reaction under solvent-free conditions gave two kinds of aromatic acids coming from different moieties of α,β-epoxy ketone via the further oxidation of aromatic aldehyde. The substituent effect was discussed, and the reaction mechanism was proposed. This method allowed the reaction to occur in a simple system metal-free. American Chemical Society 2022-06-10 /pmc/articles/PMC9245109/ /pubmed/35785280 http://dx.doi.org/10.1021/acsomega.2c01464 Text en © 2022 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Jiang, Bing Li, Huai-Zhu Li, Rui-Jun Zhang, Jianye Zhang, Yun-Xiao Selective Oxidative Cleavage of the C–C Bond in α,β-Epoxy Ketone into Carbonyl Compounds |
title | Selective Oxidative Cleavage of the C–C Bond
in α,β-Epoxy Ketone into Carbonyl Compounds |
title_full | Selective Oxidative Cleavage of the C–C Bond
in α,β-Epoxy Ketone into Carbonyl Compounds |
title_fullStr | Selective Oxidative Cleavage of the C–C Bond
in α,β-Epoxy Ketone into Carbonyl Compounds |
title_full_unstemmed | Selective Oxidative Cleavage of the C–C Bond
in α,β-Epoxy Ketone into Carbonyl Compounds |
title_short | Selective Oxidative Cleavage of the C–C Bond
in α,β-Epoxy Ketone into Carbonyl Compounds |
title_sort | selective oxidative cleavage of the c–c bond
in α,β-epoxy ketone into carbonyl compounds |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9245109/ https://www.ncbi.nlm.nih.gov/pubmed/35785280 http://dx.doi.org/10.1021/acsomega.2c01464 |
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