Transition-Metal-Free and Site-Selective Selenylation of Heterocyclic N-Oxides in Anisole as a Green Solvent

Suk Hun Lee; Na Yeon Kwon; Ji Yoon Lee; Won An; Young Hoon Jung; Neeraj Kumar Mishra; Prithwish Ghosh; Jung Su Park; In Su Kim

doi:10.1002/ejoc.202000610

Transition-Metal-Free and Site-Selective Selenylation of Heterocyclic N-Oxides in Anisole as a Green Solvent

Suk Hun Lee
, Na Yeon Kwon
, Ji Yoon Lee
, Won An
, Young Hoon Jung
, Neeraj Kumar Mishra
, Prithwish Ghosh
, Jung Su Park
, In Su Kim

Department of Pharmacy

Sungkyunkwan University
Sookmyung Women's University

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

16 Scopus citations

Abstract

Transition-metal-free and site-selective C–H selenylation of heterocyclic N-oxides with diselenides is described. This method can be also applied for the formation of C2-sulfenylated and C2-tellurinated quinoline derivatives. Notably, the simple reaction conditions with the use of anisole as a green solvent have been employed in this coupling reaction. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process. The synthetic transformations demonstrate the utility of the developed method.

Original language	English
Pages (from-to)	4886-4892
Number of pages	7
Journal	European Journal of Organic Chemistry
Volume	2020
Issue number	31
DOIs	https://doi.org/10.1002/ejoc.202000610
State	Published - 23 Aug 2020

Keywords

Chalcogenation
Heterocycles
N-Oxides
Selenium
Transition-metal-free

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10.1002/ejoc.202000610

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title = "Transition-Metal-Free and Site-Selective Selenylation of Heterocyclic N-Oxides in Anisole as a Green Solvent",

abstract = "Transition-metal-free and site-selective C–H selenylation of heterocyclic N-oxides with diselenides is described. This method can be also applied for the formation of C2-sulfenylated and C2-tellurinated quinoline derivatives. Notably, the simple reaction conditions with the use of anisole as a green solvent have been employed in this coupling reaction. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process. The synthetic transformations demonstrate the utility of the developed method.",

keywords = "Chalcogenation, Heterocycles, N-Oxides, Selenium, Transition-metal-free",

author = "Lee, \{Suk Hun\} and Kwon, \{Na Yeon\} and Lee, \{Ji Yoon\} and Won An and Jung, \{Young Hoon\} and Mishra, \{Neeraj Kumar\} and Prithwish Ghosh and Park, \{Jung Su\} and Kim, \{In Su\}",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2020",

month = aug,

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doi = "10.1002/ejoc.202000610",

language = "English",

volume = "2020",

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journal = "European Journal of Organic Chemistry",

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TY - JOUR

T1 - Transition-Metal-Free and Site-Selective Selenylation of Heterocyclic N-Oxides in Anisole as a Green Solvent

AU - Lee, Suk Hun

AU - Kwon, Na Yeon

AU - Lee, Ji Yoon

AU - An, Won

AU - Jung, Young Hoon

AU - Mishra, Neeraj Kumar

AU - Ghosh, Prithwish

AU - Park, Jung Su

AU - Kim, In Su

PY - 2020/8/23

Y1 - 2020/8/23

N2 - Transition-metal-free and site-selective C–H selenylation of heterocyclic N-oxides with diselenides is described. This method can be also applied for the formation of C2-sulfenylated and C2-tellurinated quinoline derivatives. Notably, the simple reaction conditions with the use of anisole as a green solvent have been employed in this coupling reaction. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process. The synthetic transformations demonstrate the utility of the developed method.

AB - Transition-metal-free and site-selective C–H selenylation of heterocyclic N-oxides with diselenides is described. This method can be also applied for the formation of C2-sulfenylated and C2-tellurinated quinoline derivatives. Notably, the simple reaction conditions with the use of anisole as a green solvent have been employed in this coupling reaction. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process. The synthetic transformations demonstrate the utility of the developed method.

KW - Chalcogenation

KW - Heterocycles

KW - N-Oxides

KW - Selenium

KW - Transition-metal-free

UR - https://www.scopus.com/pages/publications/85086021186

U2 - 10.1002/ejoc.202000610

DO - 10.1002/ejoc.202000610

M3 - Article

AN - SCOPUS:85086021186

SN - 1434-193X

VL - 2020

SP - 4886

EP - 4892

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 31

ER -

Transition-Metal-Free and Site-Selective Selenylation of Heterocyclic N-Oxides in Anisole as a Green Solvent

Abstract

Keywords

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