The radical-based reduction with (TMS)(3)SiH 'on water'

Reduction of different organohalides, bromonucleosides among them, was successfully carried Out in yields ranging from 75% to quantitative, using (TMS)(3)SiH in a heterogeneous system with water as the solvent. Our procedure, employing 2-mercaptoethanol as the catalyst and the hydrophobic diazo-comp...

Full description

Saved in:
Bibliographic Details
Published inSynlett no. 18; pp. 2854 - 2856
Main Authors Postigo, A, Ferreri, C, Navacchia, ML, Chatgilialoglu, C
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 03.11.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
tris(trimethylsilyl)silane
REAGENT
reductions
azo compounds
AQUEOUS-MEDIA
radical reactions
REACTIVITY
CHEMISTRY
thiols
Online AccessGet more information

Cover

More Information
Summary:Reduction of different organohalides, bromonucleosides among them, was successfully carried Out in yields ranging from 75% to quantitative, using (TMS)(3)SiH in a heterogeneous system with water as the solvent. Our procedure, employing 2-mercaptoethanol as the catalyst and the hydrophobic diazo-compound ACCN as the initiator, illustrates that (TMS)(3)SiH can be the radical-based reducing agent of choice in aqueous medium. (TMS)(3)SiH does not suffer from any significant reaction with water and can safely be used with additional benefit, such as ease of purification and environmental compatibility.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2005-918917