Studies of <i>N</i>-arylation of adamantane-containing amines using Chan-Lam reaction

Abstract

Optimization of the conditions of the Chan-Lam reaction was carried out to obtain N -aryl derivatives of adamantane-containing amines. Under optimal conditions [2 equiv p -tolylboronic acid, 2 equiv. DBU, 0.1 M solution in MeCN, 20 mol % Cu(OAc)2·H2O, 25°C, 24 h] reactions with a series of adamantane-containing amines and diamines, differing by the steric hindrances at the amino group, were performed. Strong dependence of the amine reactivity on their structure was observed, the best yield of the monoamine derivatives reached 74% and that of diamines - 66%.