ChemInform Abstract: Silver(I)‐Promoted ipso‐Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate.

Abstract

Silver(I)-Promoted ipso-Nitration of Carboxylic Acids by Nitronium Tetrafluoroborate. -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 is reported. This transformation probably proceeds via an alkyl/aryl-silver intermediate, which subsequently reacts with the nitronium ion to form nitro substances. Mild reaction conditions, tolerance of a broad range of functional groups, and formation of only the ipso-nitrated products are the key features of this methodology compared to other known methods for the syntheses of nitroalkyls and nitroarenes. -(NATARAJAN*, P.; CHAUDHARY, R.; VENUGOPALAN, P.; J. Org. Chem. 80 (2015) 21, 10498-10504, http://dx.