Selenium-Epoxy ‘Click’ Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium Compounds

This work establishes the ‘click’ nature of the base-catalyzed oxirane ring opening reaction by the selenolate nucleophile. The ‘click’-generated ß-hydroxy selenide can be alkylated to afford cationic selenium species. Hemolytic studies suggest that selenonium cations do not lyse red blood cells eve...

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Main Authors: Taejun Eom, Anzar Khan
Format: Article
Language:English
Published: MDPI AG 2020-10-01
Series:Chemistry
Subjects:
Online Access:https://www.mdpi.com/2624-8549/2/4/54
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author Taejun Eom
Anzar Khan
author_facet Taejun Eom
Anzar Khan
author_sort Taejun Eom
collection DOAJ
description This work establishes the ‘click’ nature of the base-catalyzed oxirane ring opening reaction by the selenolate nucleophile. The ‘click’-generated ß-hydroxy selenide can be alkylated to afford cationic selenium species. Hemolytic studies suggest that selenonium cations do not lyse red blood cells even at high concentrations. Overall, these results indicate the future applicability of the developed organo-selenium chemistry in the preparation of a new class of cationic materials based on the seleno-ether motif.
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spelling doaj.art-055397b082d34c03aec92214192507142023-11-20T16:07:45ZengMDPI AGChemistry2624-85492020-10-012482783610.3390/chemistry2040054Selenium-Epoxy ‘Click’ Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium CompoundsTaejun Eom0Anzar Khan1Department of Chemical and Biological Engineering, Korea University, 145 Anam-Ro, Seongbuk-Gu, Seoul 02841, KoreaDepartment of Chemical and Biological Engineering, Korea University, 145 Anam-Ro, Seongbuk-Gu, Seoul 02841, KoreaThis work establishes the ‘click’ nature of the base-catalyzed oxirane ring opening reaction by the selenolate nucleophile. The ‘click’-generated ß-hydroxy selenide can be alkylated to afford cationic selenium species. Hemolytic studies suggest that selenonium cations do not lyse red blood cells even at high concentrations. Overall, these results indicate the future applicability of the developed organo-selenium chemistry in the preparation of a new class of cationic materials based on the seleno-ether motif.https://www.mdpi.com/2624-8549/2/4/54‘click’ chemistryoxirane ring opening reactionorgano-seleniumorgano-selenonium
spellingShingle Taejun Eom
Anzar Khan
Selenium-Epoxy ‘Click’ Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium Compounds
Chemistry
‘click’ chemistry
oxirane ring opening reaction
organo-selenium
organo-selenonium
title Selenium-Epoxy ‘Click’ Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium Compounds
title_full Selenium-Epoxy ‘Click’ Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium Compounds
title_fullStr Selenium-Epoxy ‘Click’ Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium Compounds
title_full_unstemmed Selenium-Epoxy ‘Click’ Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium Compounds
title_short Selenium-Epoxy ‘Click’ Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium Compounds
title_sort selenium epoxy click reaction and se alkylation efficient access to organo selenium and selenonium compounds
topic ‘click’ chemistry
oxirane ring opening reaction
organo-selenium
organo-selenonium
url https://www.mdpi.com/2624-8549/2/4/54
work_keys_str_mv AT taejuneom seleniumepoxyclickreactionandsealkylationefficientaccesstoorganoseleniumandselenoniumcompounds
AT anzarkhan seleniumepoxyclickreactionandsealkylationefficientaccesstoorganoseleniumandselenoniumcompounds