Electrophilic organic selenium reagents: protonated seleninic acids as precursors for unsymmetrical aromatic selenides

TY - JOUR

T1 - Electrophilic organic selenium reagents

T2 - protonated seleninic acids as precursors for unsymmetrical aromatic selenides

AU - Stuhr-Hansen, Nicolai

AU - Sølling, Theis Ivan

AU - Henriksen, Lars

N1 - Keywords: electrophilic selenium reagents, aryl selenides, seleninic acids, diselenides

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 - Former Faculty of Pharmaceutical Sciences

KW - Faculty of Science

U2 - 10.1016/j.tet.2011.02.004

DO - 10.1016/j.tet.2011.02.004

M3 - Journal article

SN - 0040-4020

VL - 67

SP - 2633

EP - 2643

JO - Tetrahedron

JF - Tetrahedron

IS - 14

ER -