A rapid method for efficient palladium-catalyzed N-arylation of polynitrogenated
macrocycles is presented. Its applicability for functionalization of protected azamacrocycles
of various sizes with substituted aryl bromides of optional electronic properties
is demonstrated. The compatibility of the protocol with common N-protecting schemes
as well as the impact of electronic versus steric factors is discussed. Using a commercially
available catalytic system and easily available alkoxide or phenoxide base, the method
provides moderate to excellent yields of N-arylated azamacrocycles (45–96%).
Key words
azamacrocycles - N-arylation - C–N coupling - heterocycles - homogeneous catalysis