Silver(I)-Promoted ipso-Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate
Department of Chemistry & Centre for Advanced Studies in Chemistry, Panjab University, Chandigarh 160 014, India
J. Org. Chem., 2015, 80 (21), pp 10498–10504
DOI: 10.1021/acs.joc.5b02133
Publication Date (Web): October 12, 2015
Copyright © 2015 American Chemical Society
*E-mail: pnataraj@pu.ac.in
Abstract
A novel and efficient method for the regioselective nitration of a series of aliphatic and aromatic carboxylic acids to their corresponding nitro compounds using nitronium tetrafluoroborate and silver carbonate in dimethylacetamide has been described. This transformation is believed to proceed via the alkyl-silver or aryl-silver intermediate, which subsequently reacts with the nitronium ion to form nitro substances. Mild reaction conditions, tolerant of a broad range of functional groups, and formation of only the ipso-nitrated products are the key features of this methodology when compared to known methods for syntheses of nitroalkyls and nitroarenes.
Supporting Information
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.5b02133.
- 1H and 13C spectra for all compounds prepared by the method described (PDF)
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