Chemoselective oxidative hydrolysis of EWG protected I--arylamino vinyl bromides to I--arylamino-I-a2-bromoacetones

Vinyl bromides bearing an arylamino group in the vicinal position are chemoselectively transformed into interesting I--arylamino-I-a2-bromoacetones through a straightforward oxidative hydrolysis promoted by calcium hypobromite under mild acidic conditions. Significantly, this particular combination...

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Bibliographic Details
Published in:Tetrahedron letters 2013-08, Vol.54 (33), p.4369-4372
Main Authors: Pace, Vittorio, Castoldi, Laura, HernA!iz, Maria, AlcA!ntara, Andres, Holzer, Wolfgang
Format: Article
Language:English
Subjects:
Aromatic compounds
Bearing
Bromides
Bromination
Calcium
Hydrolysis
Ketones
Tetrahedrons
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Summary:Vinyl bromides bearing an arylamino group in the vicinal position are chemoselectively transformed into interesting I--arylamino-I-a2-bromoacetones through a straightforward oxidative hydrolysis promoted by calcium hypobromite under mild acidic conditions. Significantly, this particular combination [vinyl bromides and Ca(BrO)2] avoids bromination at both the aromatic ring and activated positions in groups substituting the amine nitrogen. The usefulness of this class of brominated ketones has been shown in a Wittig homologation.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2013.05.118