Synthesis of N-aryl-aza-crown ethers via Pd-catalyzed amination reactions of aryl chlorides with aza-crown ethers

The Pd2(dba)3/P(i-BuNCH2CH2)3N () catalyst system effectively catalyzes the coupling of aza-crown ethers with electronically diverse aryl chlorides, affording N-aryl-aza-crown ethers in good yields. The Pd2(dba)3/P(i-BuNCH2)3CMe () catalyst system containing the more constrained bicyclic triaminophosphine is useful for aryl chlorides possessing base-sensitive ester, nitro, and nitrile functional groups.