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

Taejun Eom; Anzar Khan

doi:10.3390/chemistry2040054

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

Taejun Eom, Anzar Khan

Department of Chemical and Biological Engineering

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	827-836
Number of pages	10
Journal	Chemistry (Switzerland)
Volume	2
Issue number	4
DOIs	https://doi.org/10.3390/chemistry2040054
Publication status	Published - 2020 Dec

Bibliographical note

Funding Information:
Funding: This research was funded by National Research Foundation of Korea grant funded by the Korean government (MSIP) (NRF-18R1D1A1B07048527).

Publisher Copyright:
© 2020 by the authors. Licensee MDPI, Basel, Switzerland.

Keywords

organo-selenium
organo-selenonium
oxirane ring opening reaction
‘click’ chemistry

ASJC Scopus subject areas

Electrochemistry
Inorganic Chemistry
Organic Chemistry
Chemistry (miscellaneous)

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10.3390/chemistry2040054

Cite this

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title = "Selenium-Epoxy {\textquoteleft}Click{\textquoteright} Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium Compounds",

abstract = "This work establishes the {\textquoteleft}click{\textquoteright} nature of the base-catalyzed oxirane ring opening reaction by the selenolate nucleophile. The {\textquoteleft}click{\textquoteright}-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.",

keywords = "organo-selenium, organo-selenonium, oxirane ring opening reaction, {\textquoteleft}click{\textquoteright} chemistry",

author = "Taejun Eom and Anzar Khan",

note = "Funding Information: Funding: This research was funded by National Research Foundation of Korea grant funded by the Korean government (MSIP) (NRF-18R1D1A1B07048527). Publisher Copyright: {\textcopyright} 2020 by the authors. Licensee MDPI, Basel, Switzerland.",

year = "2020",

month = dec,

doi = "10.3390/chemistry2040054",

language = "English",

volume = "2",

pages = "827--836",

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T1 - Selenium-Epoxy ‘Click’ Reaction and Se-Alkylation—Efficient Access to Organo-Selenium and Selenonium Compounds

AU - Eom, Taejun

AU - Khan, Anzar

N1 - Funding Information: Funding: This research was funded by National Research Foundation of Korea grant funded by the Korean government (MSIP) (NRF-18R1D1A1B07048527). Publisher Copyright: © 2020 by the authors. Licensee MDPI, Basel, Switzerland.

PY - 2020/12

Y1 - 2020/12

N2 - 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.

AB - 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.

KW - organo-selenium

KW - organo-selenonium

KW - oxirane ring opening reaction

KW - ‘click’ chemistry

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DO - 10.3390/chemistry2040054

M3 - Article

AN - SCOPUS:85096204618

SN - 2624-8549

VL - 2

SP - 827

EP - 836

JO - Chemistry (Switzerland)

JF - Chemistry (Switzerland)

IS - 4

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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