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Two dimensional inorganic electride-promoted electron transfer efficiency in transfer hydrogenation of alkynes and alkenes

A simple and highly efficient transfer hydrogenation of alkynes and alkenes by using a two-dimensional electride, dicalcium nitride ([Ca(2)N](+)·e(–)), as an electron transfer agent is disclosed. Excellent yields in the transformation are attributed to the remarkable electron transfer efficiency in...

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Autores principales: Kim, Ye Ji, Kim, Sun Min, Cho, Eun Jin, Hosono, Hideo, Yang, Jung Woon, Kim, Sung Wng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659176/
https://www.ncbi.nlm.nih.gov/pubmed/29511519
http://dx.doi.org/10.1039/c5sc00933b
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author Kim, Ye Ji
Kim, Sun Min
Cho, Eun Jin
Hosono, Hideo
Yang, Jung Woon
Kim, Sung Wng
author_facet Kim, Ye Ji
Kim, Sun Min
Cho, Eun Jin
Hosono, Hideo
Yang, Jung Woon
Kim, Sung Wng
author_sort Kim, Ye Ji
collection PubMed
description A simple and highly efficient transfer hydrogenation of alkynes and alkenes by using a two-dimensional electride, dicalcium nitride ([Ca(2)N](+)·e(–)), as an electron transfer agent is disclosed. Excellent yields in the transformation are attributed to the remarkable electron transfer efficiency in the electride-mediated reactions. It is clarified that an effective discharge of electrons from the [Ca(2)N](+)·e(–) electride in alcoholic solvents is achieved by the decomposition of the electride via alcoholysis and the generation of ammonia and Ca(O(i)Pr)(2). We found that the choice of solvent was crucial for enhancing the electron transfer efficiency, and a maximum efficiency of 80% was achieved by using a DMF mixed isopropanol co-solvent system. This is the highest value reported to date among single electron transfer agents in the reduction of C–C multiple bonds. The observed reactivity and efficiency establish that electrides with a high density of anionic electrons can readily participate in the reduction of organic functional groups.
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spelling pubmed-56591762018-03-06 Two dimensional inorganic electride-promoted electron transfer efficiency in transfer hydrogenation of alkynes and alkenes Kim, Ye Ji Kim, Sun Min Cho, Eun Jin Hosono, Hideo Yang, Jung Woon Kim, Sung Wng Chem Sci Chemistry A simple and highly efficient transfer hydrogenation of alkynes and alkenes by using a two-dimensional electride, dicalcium nitride ([Ca(2)N](+)·e(–)), as an electron transfer agent is disclosed. Excellent yields in the transformation are attributed to the remarkable electron transfer efficiency in the electride-mediated reactions. It is clarified that an effective discharge of electrons from the [Ca(2)N](+)·e(–) electride in alcoholic solvents is achieved by the decomposition of the electride via alcoholysis and the generation of ammonia and Ca(O(i)Pr)(2). We found that the choice of solvent was crucial for enhancing the electron transfer efficiency, and a maximum efficiency of 80% was achieved by using a DMF mixed isopropanol co-solvent system. This is the highest value reported to date among single electron transfer agents in the reduction of C–C multiple bonds. The observed reactivity and efficiency establish that electrides with a high density of anionic electrons can readily participate in the reduction of organic functional groups. Royal Society of Chemistry 2015-06-01 2015-04-13 /pmc/articles/PMC5659176/ /pubmed/29511519 http://dx.doi.org/10.1039/c5sc00933b Text en This journal is © The Royal Society of Chemistry 2015 http://creativecommons.org/licenses/by/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence (CC BY 3.0)
spellingShingle Chemistry
Kim, Ye Ji
Kim, Sun Min
Cho, Eun Jin
Hosono, Hideo
Yang, Jung Woon
Kim, Sung Wng
Two dimensional inorganic electride-promoted electron transfer efficiency in transfer hydrogenation of alkynes and alkenes
title Two dimensional inorganic electride-promoted electron transfer efficiency in transfer hydrogenation of alkynes and alkenes
title_full Two dimensional inorganic electride-promoted electron transfer efficiency in transfer hydrogenation of alkynes and alkenes
title_fullStr Two dimensional inorganic electride-promoted electron transfer efficiency in transfer hydrogenation of alkynes and alkenes
title_full_unstemmed Two dimensional inorganic electride-promoted electron transfer efficiency in transfer hydrogenation of alkynes and alkenes
title_short Two dimensional inorganic electride-promoted electron transfer efficiency in transfer hydrogenation of alkynes and alkenes
title_sort two dimensional inorganic electride-promoted electron transfer efficiency in transfer hydrogenation of alkynes and alkenes
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5659176/
https://www.ncbi.nlm.nih.gov/pubmed/29511519
http://dx.doi.org/10.1039/c5sc00933b
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