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Synlett 2013; 24(5): 652-656
DOI: 10.1055/s-0032-1318216
DOI: 10.1055/s-0032-1318216
letter
Catalytic Reduction of ortho- and para-Azidonitrobenzenes via tert-Butoxide Ion Mediated Electron Transfer
Further Information
Publication History
Received: 11 January 2013
Accepted after revision: 22 January 2013
Publication Date:
06 February 2013 (online)
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
- Full experimental procedures and characterisation for compounds listed in Table 2 and for compound 19 in this article are available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
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For some selected publications regarding the radical chemistry of azides, see: