Na(2)S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products

A practical method for the deoxygenation of α-hydroxyl carbonyl compounds under mild reaction conditions is reported here. The use of cheap and easy-to-handle Na(2)S·9H(2)O as the reductant in the presence of PPh(3) and N-chlorosuccinimide (NCS) enables the selective dehydroxylation of α-hydroxyl ca...

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Detalles Bibliográficos
Autores principales: Xu, Xiaobo, Yan, Leyu, Zhang, Zhi-Kai, Lu, Bingqing, Guo, Zhuangwen, Chen, Mengyue, Cao, Zhong-Yan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9330554/
https://www.ncbi.nlm.nih.gov/pubmed/35897854
http://dx.doi.org/10.3390/molecules27154675
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author Xu, Xiaobo
Yan, Leyu
Zhang, Zhi-Kai
Lu, Bingqing
Guo, Zhuangwen
Chen, Mengyue
Cao, Zhong-Yan
author_facet Xu, Xiaobo
Yan, Leyu
Zhang, Zhi-Kai
Lu, Bingqing
Guo, Zhuangwen
Chen, Mengyue
Cao, Zhong-Yan
author_sort Xu, Xiaobo
collection PubMed
description A practical method for the deoxygenation of α-hydroxyl carbonyl compounds under mild reaction conditions is reported here. The use of cheap and easy-to-handle Na(2)S·9H(2)O as the reductant in the presence of PPh(3) and N-chlorosuccinimide (NCS) enables the selective dehydroxylation of α-hydroxyl carbonyl compounds, including ketones, esters, amides, imides and nitrile groups. The synthetic utility is demonstrated by the late-stage deoxygenation of bioactive molecule and complex natural products.
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spelling pubmed-93305542022-07-29 Na(2)S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products Xu, Xiaobo Yan, Leyu Zhang, Zhi-Kai Lu, Bingqing Guo, Zhuangwen Chen, Mengyue Cao, Zhong-Yan Molecules Article A practical method for the deoxygenation of α-hydroxyl carbonyl compounds under mild reaction conditions is reported here. The use of cheap and easy-to-handle Na(2)S·9H(2)O as the reductant in the presence of PPh(3) and N-chlorosuccinimide (NCS) enables the selective dehydroxylation of α-hydroxyl carbonyl compounds, including ketones, esters, amides, imides and nitrile groups. The synthetic utility is demonstrated by the late-stage deoxygenation of bioactive molecule and complex natural products. MDPI 2022-07-22 /pmc/articles/PMC9330554/ /pubmed/35897854 http://dx.doi.org/10.3390/molecules27154675 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Xu, Xiaobo
Yan, Leyu
Zhang, Zhi-Kai
Lu, Bingqing
Guo, Zhuangwen
Chen, Mengyue
Cao, Zhong-Yan
Na(2)S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products
title Na(2)S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products
title_full Na(2)S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products
title_fullStr Na(2)S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products
title_full_unstemmed Na(2)S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products
title_short Na(2)S-Mediated One-Pot Selective Deoxygenation of α-Hydroxyl Carbonyl Compounds including Natural Products
title_sort na(2)s-mediated one-pot selective deoxygenation of α-hydroxyl carbonyl compounds including natural products
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9330554/
https://www.ncbi.nlm.nih.gov/pubmed/35897854
http://dx.doi.org/10.3390/molecules27154675
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