4373-56-2Relevant articles and documents
Meta-Selective CAr-H Nitration of Arenes through a Ru3(CO)12-Catalyzed Ortho-Metalation Strategy
Fan, Zhoulong,Ni, Jiabin,Zhang, Ao
supporting information, p. 8470 - 8475 (2016/07/26)
The first example of transition metal-catalyzed meta-selective CAr-H nitration of arenes is described. With the use of Ru3(CO)12 as the catalyst and Cu(NO3)2·3H2O as the nitro source, a wide spectrum of arenes bearing diversified N-heterocycles or oximido as the directing groups were nitrated with meta-selectivity exclusively. Mechanism studies have demonstrated the formation of a new 18e-octahedral ruthenium species as a key ortho-CAr-H metalated intermediate, which may be responsible for the subsequent meta-selective electrophilic aromatic substitution (SEAr). Moreover, this approach provides a fast-track strategy for atom/step economical synthesis of many useful pharmaceutical molecules.
Mono-nitration of aromatic compounds via their nitric acid salts
Zhang, Pingsheng,Cedilote, Miall,Cleary, Thomas P.,Pierce, Michael E.
, p. 8659 - 8664 (2008/03/30)
Aromatic compounds bearing a basic nitrogen atom can be converted to the corresponding nitric acid salts. Mono-nitration of the compounds can be carried out by adding a dichloromethane solution of the salts to sulfuric acid, or by adding acetyl chloride (or trifluoroacetic anhydride) to a dichloromethane solution of the salts. This protocol provides, among other benefits, the most convenient and reliable way for the prevention of over-/under-nitration and is especially suitable for scale-up.
