Nitration of Strongly Deactivated Aromatics with Superacidic Mixed Nitric-Triflatoboric Acid (HNO3/2CF3SO3H-B(O3SCF3)3)

Article abstract of DOI:10.1021/jo00127a048

The nitration of various deactivated arenes (including methanesulfonyl-, nitro-, and polyhalobenzenes) was carried out in good yield with mixed nitric-triflatoboric superacid.For example pentafluorobenzene gave pentafluoronitrobenzene in 99percent yield, nitrobenzene to m-dinitrobenzene in 92percent selectivity with 85percent overall yield, and methyl phenyl sulfone gave only the m-nitro isomer in 78percent isolated yield.Thus the new nitrating system gives high regioselectivity and yields under generally mild reaction conditions.The reagent system is compatible with many functional groups of arenes.