Electrophilic organic selenium reagents - Protonated seleninic acids as precursors for unsymmetrical aromatic selenides

Nicolai Stuhr-Hansen; Theis Ivan Sølling; Lars Henriksen

doi:10.1016/j.tet.2011.02.004

Electrophilic organic selenium reagents - Protonated seleninic acids as precursors for unsymmetrical aromatic selenides

Nicolai Stuhr-Hansen^*, Theis Ivan Sølling, Lars Henriksen

^*Corresponding author for this work

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

23 Scopus citations

Abstract

Arylselenylations of methylbenzenes, methoxybenzenes and thiophene were smoothly achieved with selenenium ions generated by comproportionation of 1:1 mixtures of p-toluenesulfonic acid salts of seleninic acids and the corresponding diselenides. A series of p-toluenesulfonic salts of seleninic acids were prepared by hydrogen peroxide oxidation of the corresponding diselenides in the presence of p-toluenesulfonic acid. Novel 2-(organylseleno)thiophenes were obtained by heating the protonated seleninic acids with a 50-fold excess of thiophene in glacial acetic acid.

Original language	English
Pages (from-to)	2633-2643
Number of pages	11
Journal	Tetrahedron
Volume	67
Issue number	14
DOIs	https://doi.org/10.1016/j.tet.2011.02.004
State	Published - 8 Apr 2011
Externally published	Yes

Keywords

Aryl selenides
Diselenides
Electrophilic selenium reagents
Seleninic acids

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.02.004

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title = "Electrophilic organic selenium reagents - Protonated seleninic acids as precursors for unsymmetrical aromatic selenides",

abstract = "Arylselenylations of methylbenzenes, methoxybenzenes and thiophene were smoothly achieved with selenenium ions generated by comproportionation of 1:1 mixtures of p-toluenesulfonic acid salts of seleninic acids and the corresponding diselenides. A series of p-toluenesulfonic salts of seleninic acids were prepared by hydrogen peroxide oxidation of the corresponding diselenides in the presence of p-toluenesulfonic acid. Novel 2-(organylseleno)thiophenes were obtained by heating the protonated seleninic acids with a 50-fold excess of thiophene in glacial acetic acid.",

keywords = "Aryl selenides, Diselenides, Electrophilic selenium reagents, Seleninic acids",

author = "Nicolai Stuhr-Hansen and S{\o}lling, \{Theis Ivan\} and Lars Henriksen",

year = "2011",

month = apr,

day = "8",

doi = "10.1016/j.tet.2011.02.004",

language = "English",

volume = "67",

pages = "2633--2643",

journal = "Tetrahedron",

issn = "0040-4020",

number = "14",

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TY - JOUR

T1 - Electrophilic organic selenium reagents - Protonated seleninic acids as precursors for unsymmetrical aromatic selenides

AU - Stuhr-Hansen, Nicolai

AU - Sølling, Theis Ivan

AU - Henriksen, Lars

PY - 2011/4/8

Y1 - 2011/4/8

N2 - Arylselenylations of methylbenzenes, methoxybenzenes and thiophene were smoothly achieved with selenenium ions generated by comproportionation of 1:1 mixtures of p-toluenesulfonic acid salts of seleninic acids and the corresponding diselenides. A series of p-toluenesulfonic salts of seleninic acids were prepared by hydrogen peroxide oxidation of the corresponding diselenides in the presence of p-toluenesulfonic acid. Novel 2-(organylseleno)thiophenes were obtained by heating the protonated seleninic acids with a 50-fold excess of thiophene in glacial acetic acid.

AB - Arylselenylations of methylbenzenes, methoxybenzenes and thiophene were smoothly achieved with selenenium ions generated by comproportionation of 1:1 mixtures of p-toluenesulfonic acid salts of seleninic acids and the corresponding diselenides. A series of p-toluenesulfonic salts of seleninic acids were prepared by hydrogen peroxide oxidation of the corresponding diselenides in the presence of p-toluenesulfonic acid. Novel 2-(organylseleno)thiophenes were obtained by heating the protonated seleninic acids with a 50-fold excess of thiophene in glacial acetic acid.

KW - Aryl selenides

KW - Diselenides

KW - Electrophilic selenium reagents

KW - Seleninic acids

UR - https://www.scopus.com/pages/publications/79952574672

U2 - 10.1016/j.tet.2011.02.004

DO - 10.1016/j.tet.2011.02.004

M3 - Article

AN - SCOPUS:79952574672

SN - 0040-4020

VL - 67

SP - 2633

EP - 2643

JO - Tetrahedron

JF - Tetrahedron

IS - 14

ER -

Electrophilic organic selenium reagents - Protonated seleninic acids as precursors for unsymmetrical aromatic selenides

Abstract

Keywords

ASJC Scopus subject areas

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