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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...

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Autores principales: Jiang, Bing, Li, Huai-Zhu, Li, Rui-Jun, Zhang, Jianye, Zhang, Yun-Xiao
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2022
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.
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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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