Synlett 2013; 24(5): 652-656
DOI: 10.1055/s-0032-1318216
letter
© Georg Thieme Verlag Stuttgart · New York

Catalytic Reduction of ortho- and para-Azidonitrobenzenes via tert-Butoxide Ion Mediated Electron Transfer

James Burnley
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK   Fax: +44(115)9513533   eMail: john.moses@nottingham.ac.uk
,
Giorgio Carbone
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK   Fax: +44(115)9513533   eMail: john.moses@nottingham.ac.uk
,
John E. Moses*
School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD, UK   Fax: +44(115)9513533   eMail: john.moses@nottingham.ac.uk
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Publikationsverlauf

Received: 11. Januar 2013

Accepted after revision: 22. Januar 2013

Publikationsdatum:
06. Februar 2013 (eFirst)

Abstract

The reduction of a range of substituted azidonitrobenzene derivatives to the corresponding aniline is described. The chemoselective reaction proceeds cleanly and in good yield, generating minimal waste products. The process involves a thiazolium salt derived species which is proposed as a radical anion relay, with tert-butoxide as the stoichiometric reductant.

Supporting Information

 
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