37385-00-5Relevant academic research and scientific papers
Ligand-free Iron(II)-Catalyzed N-Alkylation of Hindered Secondary Arylamines with Non-activated Secondary and Primary Alcohols via a Carbocationic Pathway
Nayal, Onkar S.,Thakur, Maheshwar S.,Kumar, Manoranjan,Kumar, Neeraj,Maurya, Sushil K.
supporting information, p. 730 - 737 (2017/12/26)
Secondary benzylic alcohols represent a challenging class of substrates for N-alkylation of amines. Herein, we describe an iron(II)-catalyzed eco-friendly protocol for N-alkylation of secondary arylamines with secondary benzyl alcohols through a carbocationic pathway instead of the known borrowing hydrogen transfer (BHT) approach. Transiently generated carbocations, produced from alcohols via self-condensation, were coupled with arylamines to provide highly functionalized amine products. The scope of this methodology involves N-alkylation of primary, secondary and heterocyclic amines with primary/secondary benzylic, allylic and heterocyclic alcohols, which are common key structures in numerous pharmaceuticals drugs. The method can also be easily adopted for the amination of various natural products. (Figure presented.).
Palladium-catalyzed microwave-assisted amination of 1-bromonaphthalenes and 5-and 8-bromoquinolines
Wang, Tammy,Magnin, David R.,Hamann, Lawrence G.
, p. 897 - 900 (2007/10/03)
1-Aminonaphthalenes and 5-and 8-aminoquinolines were rapidly prepared from the respective aryl bromides in good yields by Pd-catalyzed aryl amination under microwave conditions. Consistent improvements in yields over those obtained under standard conditions were seen with quinoline substrates. In the cases where 5-bromo-8-cyanoquinoline was used as a substrate, no desired products were obtained under standard conditions with a number of different primary and secondary amines. However, microwave conditions provided the desired products in good to excellent yields.
