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Efficient Protocol for Synthesis of β‐Hydroxy(alkoxy)selenides via Electrochemical Iodide‐Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides
An efficient protocol for the synthesis of β‐hydroxy(alkoxy)selenides was developed through the electrochemical iodide‐catalyzed oxyselenation of styrene derivatives with dialkyl(aryl)diselenides under mild reaction conditions. Mechanistic studies showed that the cation I(+) is involved during the w...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6769433/ https://www.ncbi.nlm.nih.gov/pubmed/31592067 http://dx.doi.org/10.1002/open.201900246 |
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author | Chen, Jinyang Mei, Lan Wang, Haiying Hu, Li Sun, Xiaorui Shi, Jianwei Li, Qiang |
author_facet | Chen, Jinyang Mei, Lan Wang, Haiying Hu, Li Sun, Xiaorui Shi, Jianwei Li, Qiang |
author_sort | Chen, Jinyang |
collection | PubMed |
description | An efficient protocol for the synthesis of β‐hydroxy(alkoxy)selenides was developed through the electrochemical iodide‐catalyzed oxyselenation of styrene derivatives with dialkyl(aryl)diselenides under mild reaction conditions. Mechanistic studies showed that the cation I(+) is involved during the whole process, and accelerates the formation of seleniranium ion via substitution and addition reaction with dialkyl(aryl)diselenides and styrene derivatives. The corresponding products are formed in good to excellent yields. This electrochemical oxyselenation provides an efficient strategy for difunctionalization of alkenes. |
format | Online Article Text |
id | pubmed-6769433 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-67694332019-10-07 Efficient Protocol for Synthesis of β‐Hydroxy(alkoxy)selenides via Electrochemical Iodide‐Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides Chen, Jinyang Mei, Lan Wang, Haiying Hu, Li Sun, Xiaorui Shi, Jianwei Li, Qiang ChemistryOpen Communications An efficient protocol for the synthesis of β‐hydroxy(alkoxy)selenides was developed through the electrochemical iodide‐catalyzed oxyselenation of styrene derivatives with dialkyl(aryl)diselenides under mild reaction conditions. Mechanistic studies showed that the cation I(+) is involved during the whole process, and accelerates the formation of seleniranium ion via substitution and addition reaction with dialkyl(aryl)diselenides and styrene derivatives. The corresponding products are formed in good to excellent yields. This electrochemical oxyselenation provides an efficient strategy for difunctionalization of alkenes. John Wiley and Sons Inc. 2019-09-10 /pmc/articles/PMC6769433/ /pubmed/31592067 http://dx.doi.org/10.1002/open.201900246 Text en ©2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Communications Chen, Jinyang Mei, Lan Wang, Haiying Hu, Li Sun, Xiaorui Shi, Jianwei Li, Qiang Efficient Protocol for Synthesis of β‐Hydroxy(alkoxy)selenides via Electrochemical Iodide‐Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides |
title | Efficient Protocol for Synthesis of β‐Hydroxy(alkoxy)selenides via Electrochemical Iodide‐Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides |
title_full | Efficient Protocol for Synthesis of β‐Hydroxy(alkoxy)selenides via Electrochemical Iodide‐Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides |
title_fullStr | Efficient Protocol for Synthesis of β‐Hydroxy(alkoxy)selenides via Electrochemical Iodide‐Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides |
title_full_unstemmed | Efficient Protocol for Synthesis of β‐Hydroxy(alkoxy)selenides via Electrochemical Iodide‐Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides |
title_short | Efficient Protocol for Synthesis of β‐Hydroxy(alkoxy)selenides via Electrochemical Iodide‐Catalyzed Oxyselenation of Styrene Derivatives with Dialkyl(aryl)diselenides |
title_sort | efficient protocol for synthesis of β‐hydroxy(alkoxy)selenides via electrochemical iodide‐catalyzed oxyselenation of styrene derivatives with dialkyl(aryl)diselenides |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6769433/ https://www.ncbi.nlm.nih.gov/pubmed/31592067 http://dx.doi.org/10.1002/open.201900246 |
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