Ga. Olah et al., NITRATION OF STRONGLY DEACTIVATED AROMATICS WITH SUPERACIDIC MIXED NITRIC-TRIFLATOBORIC ACID (HNO3 2CF(3)SO(3)H-B(O3SCF3)(3))/, Journal of organic chemistry, 60(22), 1995, pp. 7348-7350
The nitration of various deactivated arenes (including methanesulfonyl
-, nitro-, and polyhalobenzenes) was carried out in good yield with mi
xed nitric-triflatoboric superacid. For example pentafluorobenzene gav
e pentafluoronitrobenzene in 99% yield, nitrobenzene to m-dinitrobenze
ne in 92% selectivity with 85% overall yield, and methyl phenyl sulfon
e gave only the m-nitro isomer in 78% isolated yield. Thus the new nit
rating system gives high regioselectivity and yields under generally m
ild reaction conditions. The reagent system is compatible with many fu
nctional groups of arenes.