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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...

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Autores principales: Chen, Jinyang, Mei, Lan, Wang, Haiying, Hu, Li, Sun, Xiaorui, Shi, Jianwei, Li, Qiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
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.
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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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