Journal of Organic Chemistry p. 7348 - 7350 (1995)
Update date:2022-08-03
Topics:
Olah, George A.
Orlinkov, Alexander
Oxyzoglou, Alexandros B.
Prakash, G. k. Surya
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.
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