Cu-Catalyzed/Mediated Synthesis Of N-Fluoroalkylanilines

Aromatic amines are core units of a great number of natural or unnatural bio-active molecules.The introduction of strongly electron-withdrawing groups such as 2,2,2-trifluoroethyl group to the aromatic amines can greatly improve their metabolic stability.This dissertation describes my study in the development of general and efficient methods for the synthesis of fluoroalkylated aromatic amines from readily available reagents,and can be divided into the following two parts:1.Preparation of fluoroalkylarylamines under Cham-Lam reaction conditions Under copper-catalyzed/promoted conditions,we applied the Chan-Lam reaction for the first time to achieve the oxidative coupling reaction of aromatic boronic acid with trifluoroethylamine or difluoroethylamine under relatively mild conditions,The difference of the fluoroalkylamines in reactivity was also found.The reaction has the following merits: a)does not require a strict degassing process;b)the aromatic boronic acids are relatively inexpensive;c)the substrate scope is broad.2.Preparation of fluoroalkylarylamines under Ul mann reaction conditions We use the Ullmann reaction to achieve the preparation of a fluoroalkylarylamines under relatively mild conditions.This reaction has the following advantages: a)inexpensive and readily available reagents;b)no using of dry solvent;c)operationally simple;d)suitable for the heteroaromatic substrates.