Nitration Alternative

13 December 2004

There are times when aromatic nitration is desired, but the conditions for the nitration reaction are not compatible with other functionality in the molecule and/or the regiochemistry of the nitration is difficult to control. A recent publication from Olah’s group* describes the use of boronic acids (increasingly common synthetic intermediates thanks to Professor Suzuki) as masked nitro groups.

The reaction is an ipso-nitration, using inorganic nitrate salts and trimethylsilylchloride, and proceeds in generally high yield. The conditions are mild, and the workup is easy.

Compatibility with a limited range of other functional groups was demonstrated.

* G. Olah et al., Org. Letts, 2004, 6, 2205-2207.