Chan–Lam N -Arylation of Adamantane-Containing Amines

The Chan–Lam reaction conditions were optimized for the synthesis of N -aryl derivatives of adamantane-containing amines. A number of adamantane-containing amines and diamines with different steric hindrances at the primary amino groups were reacted with p -tolylboronic acid under the optimized conditions [0.1 M solution of amine in MeCN, p -tolylboronic acid (2 equiv), DBU (2 equiv), copper(II) acetate (20 mol %), 25°C, 24 h]. The reactivity of the amines was found to strongly depend on their structure, and the maximum yield of the target products reached 74% from the monoamines and 66% from the diamines.