Oligomeric iodosylbenzene sulfate: A convenient hypervalent iodine reagent for oxidation of organic sulfides and alkenes

Результат исследований: Материалы для журналаСтатья

21 Цитирования (Scopus)

Выдержка

Oligomeric iodosylbenzene sulfate, (PhIO)3·SO 3, which can be formally considered as a partially depolymerized activated iodosylbenzene, is a readily available, stable, and water-soluble hypervalent iodine reagent that is useful for the oxidation of sulfides or alkenes. Furthermore, this reagent can be conveniently generated in situ from (diacetoxyiodo)benzene and sodium bisulfate and used without isolation in oxidations in aqueous solution or under solvent-free conditions. The reaction of iodosylbenzene sulfate in situ with organic sulfides at room temperature affords sulfoxides in high yields without over-oxidation to sulfones, and this reaction is compatible with the presence in the substrate molecule of hydroxy groups, double bonds, benzylic carbon atoms, carboxylate groups, and various substituted phenyl rings. The reaction of an alkene with iodosylbenzene sulfate generated in situ results in oxidative rearrangement to form a ketone or aldehyde.

Язык оригиналаАнглийский
Номер статьиM01009SS
Страницы (с-по)2505-2508
Число страниц4
ЖурналSynthesis
Номер выпуска15
DOI
СостояниеОпубликовано - 1 авг 2009

Отпечаток

Alkenes
Sulfides
Iodine
Sulfates
Olefins
Oxidation
Sulfoxides
Aldehydes
Ketones
Sulfones
Benzene
Sodium
Atoms
Molecules
Carbon
Substrates
iodosobenzene
Water
Temperature

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Цитировать

Oligomeric iodosylbenzene sulfate : A convenient hypervalent iodine reagent for oxidation of organic sulfides and alkenes. / Yusubov, Mehman S.; Yusubova, Rosa Y.; Funk, Tatyana V.; Chi, Ki Whan; Zhdankin, Viktor Vladimirovich.

В: Synthesis, № 15, M01009SS, 01.08.2009, стр. 2505-2508.

Результат исследований: Материалы для журналаСтатья

@article{64c29dfbea314b058d58515347007f43,
title = "Oligomeric iodosylbenzene sulfate: A convenient hypervalent iodine reagent for oxidation of organic sulfides and alkenes",
abstract = "Oligomeric iodosylbenzene sulfate, (PhIO)3·SO 3, which can be formally considered as a partially depolymerized activated iodosylbenzene, is a readily available, stable, and water-soluble hypervalent iodine reagent that is useful for the oxidation of sulfides or alkenes. Furthermore, this reagent can be conveniently generated in situ from (diacetoxyiodo)benzene and sodium bisulfate and used without isolation in oxidations in aqueous solution or under solvent-free conditions. The reaction of iodosylbenzene sulfate in situ with organic sulfides at room temperature affords sulfoxides in high yields without over-oxidation to sulfones, and this reaction is compatible with the presence in the substrate molecule of hydroxy groups, double bonds, benzylic carbon atoms, carboxylate groups, and various substituted phenyl rings. The reaction of an alkene with iodosylbenzene sulfate generated in situ results in oxidative rearrangement to form a ketone or aldehyde.",
keywords = "(diacetoxyiodo) benzene, Hypervalent iodine, Iodine, Iodosylbenzene, Oxidations, Sulfoxides",
author = "Yusubov, {Mehman S.} and Yusubova, {Rosa Y.} and Funk, {Tatyana V.} and Chi, {Ki Whan} and Zhdankin, {Viktor Vladimirovich}",
year = "2009",
month = "8",
day = "1",
doi = "10.1055/s-0029-1216870",
language = "English",
pages = "2505--2508",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "15",

}

TY - JOUR

T1 - Oligomeric iodosylbenzene sulfate

T2 - A convenient hypervalent iodine reagent for oxidation of organic sulfides and alkenes

AU - Yusubov, Mehman S.

AU - Yusubova, Rosa Y.

AU - Funk, Tatyana V.

AU - Chi, Ki Whan

AU - Zhdankin, Viktor Vladimirovich

PY - 2009/8/1

Y1 - 2009/8/1

N2 - Oligomeric iodosylbenzene sulfate, (PhIO)3·SO 3, which can be formally considered as a partially depolymerized activated iodosylbenzene, is a readily available, stable, and water-soluble hypervalent iodine reagent that is useful for the oxidation of sulfides or alkenes. Furthermore, this reagent can be conveniently generated in situ from (diacetoxyiodo)benzene and sodium bisulfate and used without isolation in oxidations in aqueous solution or under solvent-free conditions. The reaction of iodosylbenzene sulfate in situ with organic sulfides at room temperature affords sulfoxides in high yields without over-oxidation to sulfones, and this reaction is compatible with the presence in the substrate molecule of hydroxy groups, double bonds, benzylic carbon atoms, carboxylate groups, and various substituted phenyl rings. The reaction of an alkene with iodosylbenzene sulfate generated in situ results in oxidative rearrangement to form a ketone or aldehyde.

AB - Oligomeric iodosylbenzene sulfate, (PhIO)3·SO 3, which can be formally considered as a partially depolymerized activated iodosylbenzene, is a readily available, stable, and water-soluble hypervalent iodine reagent that is useful for the oxidation of sulfides or alkenes. Furthermore, this reagent can be conveniently generated in situ from (diacetoxyiodo)benzene and sodium bisulfate and used without isolation in oxidations in aqueous solution or under solvent-free conditions. The reaction of iodosylbenzene sulfate in situ with organic sulfides at room temperature affords sulfoxides in high yields without over-oxidation to sulfones, and this reaction is compatible with the presence in the substrate molecule of hydroxy groups, double bonds, benzylic carbon atoms, carboxylate groups, and various substituted phenyl rings. The reaction of an alkene with iodosylbenzene sulfate generated in situ results in oxidative rearrangement to form a ketone or aldehyde.

KW - (diacetoxyiodo) benzene

KW - Hypervalent iodine

KW - Iodine

KW - Iodosylbenzene

KW - Oxidations

KW - Sulfoxides

UR - http://www.scopus.com/inward/record.url?scp=69749108211&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=69749108211&partnerID=8YFLogxK

U2 - 10.1055/s-0029-1216870

DO - 10.1055/s-0029-1216870

M3 - Article

AN - SCOPUS:69749108211

SP - 2505

EP - 2508

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 15

M1 - M01009SS

ER -